My Successful Lady
by xoxo-coco
Summary: Based loosely on My Fair Lady. Blair was to be successful and Chuck wants to redeem himself from his bad boy image for the board. If they can help each other everyone will be happy, there might even be something more to come from this arrangement. AU C/B
1. Friendly Agreements

**I do not own Gossip Girl or My Fair Lady.**

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Blair sat on the corner eating her sandwich and watching the nightly call girls. She was waiting for the bus to come to take her to her small apartment in Brooklyn. Her friend Serena came sat with her. Blair had just gotten off of work at the small diner not far from the corner. She didn't make much money but she was saving to go to Yale, she dreamed of being a successful business woman. She was working to take care of her mother who was suffering from dementia. She'd just finished high school and just wanted to go to college to make something of herself.  
Serena was also poor but she worked on the corner to get by. She had a rough childhood with many step fathers and an absent mother. Lily Van Der Woodsen left her daughter and her son Eric Van Der Woodsen alone with her many husbands and they would abuse the children instead of actually watch them.

Blair and Serena were best friends and helped each other whenever they could. Blair wanted to be powerful and Serena wanted to be famous. They were going to help each other get to where they wanted to be. Blair had just finished her sandwich as Serena told her about one of her clients that was very rich and cute, whom she like a lot, when a sleek black limo pulled up in front of them.

Chuck and Nate where riding around looking of entertainment for the night. It had been a long day and they needed to unwind. Chuck had to get the board of Bass Industries after they found out about Eva. She was the closest thing to a girlfriend Chuck Bass ever had, and the board was happy until the scandal broke out that she was a prostitute.

Nate and the Spectator were behind on the news of the Upper East Side. He would've been the first to report about Eva being a prostitute but he and Chuck have been best friends since they were children, he couldn't do that to him. So he was the second to report the news after having Chuck's blessing but that wasn't enough to get him more readers. He had the inside exclusives of Chuck Bass' live and famous parties but with Chuck's wild partying ways being frowned upon by the board they were becoming less and less. He need a miracle to happen like Chuck Bass having a girlfriend.

They were pulling up on the corner where Nate's favorite girl Serena worked, Nate had a crush on her but he was so busy with the Spectator that he didn't have time for a girl friend and he wasn't sure if Serena liked him back. She was a prostitute but he knew of her hard life and how she was struggling. He would pay her double and buy her gifts and things she needed. Nate was more than happy to be seeing Serena tonight, he was going to ask her to stay the weekend. He noticed that Serena was talking to a brunette girl and turned to Chuck. "Hey man, Serena has a friend. She's not blonde but I'm sure she'll do for the night."

Chuck looked at the brunette that Nate was referring to. She was about five foot five, had chocolate-brown curls that hung to the middle of her back. She was dressed in a pink polo shirt and a blue skirt, it wasn't anything slutty but it made Chuck hard just looking at her. She had her face turned away from them talking to Serena but Chuck was anxious to she Serena's mystery friend's face.

Serena noticed that limo right away. "Oh look that's him right there. It looks like he has Chuck with him tonight."

"Who's Chuck?" Blair asked.

"Nate's best friend."

Just then the window rolled down and both girls turned to the limo. Nate called out to Serena, "Hey beautiful."

She smiled brightly, "Hey yourself handsome. What's on the menu for tonight?"

"Well I was actually thinking we'd get lost this weekend, I had a very hard day at the office today."

"Sure thing Natey." Serena grabbed Blair and pulled her into the limo before she could even protect.

Serena jump into the seat next to Nate and kissed him, like they were just a regular couple. Nate was the only one allowed to kiss her. Blair however landed face first into someone's lap. Her mouth came into full contact with what she could only assume was someone's cock and from what Serena told her earlier she guessed it belonged to Chuck.

Blair looked up to meet a shocked Chuck's face. He quickly masked his emotions though and looked down at Blair. She was beautiful, her lips were ruby and pouty. Chuck just wanted to kiss them. Her eyes were big and brown, he got lost into them. She looked like a porcelain doll.  
Chuck snapped out of his observing to pull Blair up off her knees of the limo floor and on to the seat next to him. "Well that's quite the first impression", he said with his signature smirk. "I'm Chuck -"

As soon as he smirked Blair knew she knew him. He was always in the newspapers for his womanizing ways and wild parties, and because of his billion dollar company. He was a powerful man who just took it for granted. He was a play boy. Blair took this opportunity to tell him just what an ass he was was. "Bass", she finished for him. "I know exactly who you are."

"Oh do you now, I'm not surprised. I am very well-known." He smiled.

"You're known for sleeping around, boozing, and doing other debauchery."

"What's wrong with that?" Chuck asked genuinely curious. Nate and Serena were just looking at their friends with amused looks on their faces.

"What's wrong with that?! You have the potential to be much more powerful than you are but you choose to waste your money and influence on nonsense!"

"Says the hooker."

"I am not a hooker!"

"Then please enlighten me. What is it that you do?"

Blair looked down at her lap while Serena looked away and Nate and Chuck looked at her. "I'm a waitress", she said quietly. Nate busted into laughter while Blair lifted her head high holding back the tears. Chuck then noticed the name tag on her shirt. "Well Blair, I'm sure bringing people their food and cleaning tables really qualifies you to give me advice on how to be a powerful and respectable man."

Just then Nate had an idea. "Wait a minute, Chuck she's right."

Chuck glared at his friend, "What do you mean she's right Nathaniel? She has no idea what she's talking about.

"Chuck the board told you the exact same thing."

"Okay they did, but so what?"

"Blair can help you."

"The only way the waitress can help me is on her knees or in my kitchen." He turned to Blair, "Which would you prefer?"

Blair turned bright red, "Neither! I want nothing to do with you, you Basstard. I may just be a waitress but I'm smarter than you and if given the chance I'd be just as powerful as you if not more."

Nate shook his head and put his face in his hands. "Chuck would you just please be nice."

"I play nice, in the bedroom... sometimes."

"You're a heinous man, you're going to lose your Empire and have nothing" Blair said to Chuck.

Chuck turned to her with a hard look, "What are you even doing here? If you aren't going to get me off you can get out of my limo!"

"Fine!" Blair screamed.

Serena looked to Nate with a pleading look, "Nate stop him please, she's my best friend. Don't let him kick her out on the street."

Nate looked to his best friend with a sigh, "Chuck man look, she could help the both of us."

"How could she possibly help us Nathaniel? Please elaborate."

"Okay just hear me out on this." Nate took a deep breath. "You need to impress the board and improve your ways right?"

"Yes Nathaniel, I'm aware of this. Get to the point."

"Well the point is having a girlfriend would do that."

Chuck glared at Nate, "I'm Chuck Bass, I don't do girlfriends! Even if I did why would I choose a waitress?"

"You have enough money and power to turn her into a powerful business woman. A woman who the board members would love to see you with."

Chuck looked at Blair, who was watching them and hanging on to their conversation. "Why would I want to tie myself down exactly?"

"Because from the way things are looking you're going to lose Bass Industries and if that happens you won't have much money to party with."

Chuck thought about that, he knew Nate was right. Serena who was quiet the whole time turned to Nate and asked, "How does this help you?

Chuck looked at Nate and waited for an answer too. "Well the personal details of Chuck Bass' personal life will have all of Manhattan reading the Spectator. Chuck Bass with a girlfriend, no one will see it coming."

"Does that mean that we can be together if this goes well?" Serena asked hopefully.

Nate smiled, she actually wanted to be with him. "Yes, if things go well and as I hope it will Serena I would love for you to be my girlfriend."

Chuck looked between his friend and Serena and he looked down to his lap. They were in love, and they needed him to put his womanizing aside to be together. He loved Nate like a brother and would do anything for him, and if that meant having a girlfriend he'd do it. Especially since it would be helping him in the process.

Chuck looked at Blair who was looking at Nate and Serena. She wanted someone to look at her that way. She wanted to be in love like her friend was. There were a lot of things she wanted. Blair wanted to sleep in a big bed and lay on someone's chest while they played with her hair. She wanted to eat macarons before bed while he drank a glass of scotch. She wanted to have a closet full of clothes, jewelry, shoes, and purses. She wanted a powerful man to hold her at night and make her feel safe. She wanted to fix someone's tie in the morning before they headed to the office. There was just so much she wanted, but it all seemed like a dream. She was just a waitress barely getting by but if pretending to be an asshole's girlfriend would give her friend the chance she needed to be with the man she loved, she'd do it.

She looked at Chuck to see him looking at her. "Well I'm willing to do this if you are, but there must be some rules."

"Rules?" Chuck looked to Nate and Serena and sighed, "Fine rules."

"I want to go to Yale, and I'm going to need somewhere for my mother to stay."

"Yale, fine. That'll look good with the board. As for your mother, I own a hotel she can stay at the Empire everything on me."

"Where will I stay?" Blair asked quietly.

"You'll stay with me of course. If you're going to be my girlfriend you're going to have to be groomed and taught my lifestyle."

"I have to stay close to my mother, she's sick and she doesn't have anyone else."

Chuck sighed and rolled his eyes, "She can stay with us in the penthouse there are plenty of rooms, and since you won't be working anymore I'll pay for anything your mother needs."

Blair smiled at this. Eleanor would have everything she needed and Blair will be attending Yale. "One more question for the night."

Chuck waited for the question. Blair went on, "Will I have my own room?"

Chuck laughed. "Blair dear", he said in a mocking way "you will be staying in the master bed room with me."

Blair looked down and told herself she could do this. Serena's happiness, her dreams, and her mother's security rested on this.

"Fine but I won't sleep with you."

"I'm your boyfriend, you will but I promise you that you'll want it before we make hot passionate love."

Blair scoffed, "Okay take me home now."

Chuck pressed the button for the speaker to Arthur. "Arthur let's bring Mr. Archibald and his guest home then we're going to go to Ms. Blair's and collect her mother and a few things."

"Yes sir", Arthur replied faithfully.

Blair looked at him questionably, "Why tonight, it's late?"

"We're going to get started as soon as possible, we have a lot to cover before you meet the board or go off to Yale."

Blair just nodded and sat back. Serena and Nate looked excited as the limo dropped them off at Nate's. Blair was feeling nervous about being alone with Chuck, especially since they just met. Blair told Arthur her address and they were off to her apartment building.

Chuck just sat quietly looking out the window the whole ride. When they finally arrived he finally spoke. "Please be quick, I'm rather tired. Just pack clothes for tonight and tomorrow and I'll send someone over to get the rest of your things tomorrow."

"That won't be necessary, I'll just get my mother."

"Fine, that would be best. You can go shopping for you and your mother tomorrow morning while I'm at the office. Just go get her, and I'll call and have one of the guest bedrooms set up for her and have a nurse to come and sit with her if that's necessary..."

"Thank you but she has a nurse already."

Blair got out of the limo and went up to her apartment. She greeted the nurse, "Hey sorry I'm late but something important came up. I'd like to talk to you about that."

"It's no problem Miss Blair", her mother's nurse Dorota answered.

"Dorota my mother and I are going to be moving and I'd like to know if you'd work with her there."

"Of course Miss Blair, Miss Eleanor is good to watch."

"Thank you Dorota, but could you do me a favor and help me get my mother into the limo downstairs?"

Dorota looked confused, "Limo? Why you take Miss Eleanor in middle of night?" Her mother's nurse, who was like a second mother to her, raised her eyebrow in a questioning manner.

"Dorota I really don't have time to explain but I'm taking my mother somewhere nice."

"I know you're up to something and I find out."

"Okay well you can find out at a later time, just help me get my mother downstairs and in to the limo."

Dorota dropped it for now and helped Blair get the angry Eleanor into the limo. Chuck looked amused as Eleanor fought with her daughter and the nurse for having her out in her night-gown and robe. Once they were in the limo Chuck rolled down the window and spoke to Dorota.

"Hello I'm Charles Bass, Blair's boyfriend" Chuck looked to Blair "I'll be taking Blair and her mother to live with me at the Empire and I'd appreciate if you'd come to watch over her dear mother. I'd pay you double your salary now of course."

Dorota looked at Chuck suspiciously, "I don't know."

"I promise you..." Chuck waited for a name.

"Dorota."

"Dorota, Blair and her mother are in great hands. I'll make sure they are both well taken care of. You can see to that yourself."

"I be there 7 am sharp."

"Okay, well I leave for the office at 6 so I'll have Blair call you up or tell security you're coming. Thank you for accepting my offer." Chuck kissed the back of Dorota's hand.

Dorota smiled at Chuck then at Blair. "Bye Miss Blair, Mister Chuck." Then she turned and walked away.

Chuck rolled the window up once they saw that Dorota was safely in her car. Chuck then turned to Eleanor who was sound asleep. "What's wrong with her?"

"Dementia", Blair said sadly.

Chuck just nodded and took off his coat and draped it over Eleanor. Blair looked down into her lap and blushed, "Thank you."

"You're welcome Blair, it's the least I can do. You're my girlfriend now, it's my job to keep you safe and take care of you. Pretend or not, now let's go home."

They drove to the Empire in silence. When they pulled up to the hotel Blair was in awe.


	2. Intrigued

Blair was still staring at the building while Chuck was ushering Eleanor through the doors. He turned around to Blair, "Are you coming up or what? The inside is just as grand as the out."

Blair looked at him and smiled as she followed him and her mother into the elevator. He hit the button for the penthouse and took a gold card with a monogrammed P out his pocket and slid it into the card slot. "I'll have one made for you and Dorota", he said without looking at her.  
Blair just nodded even though he could see her. As the elevator went up Blair got more and more nervous, when the doors finally opened she felt her heart drop.

The penthouse was luxurious, Blair stepped out the elevator and was frozen in her spot. In front of her was a motorcycle with BASS on the license plate. There was a pool table with CB etched onto all the balls, next to it was a personal bar that was lit up. There was a big screen tv in front of an orange sofa that looked sofa and comfortable. The wood floors were polished and shining. Blair was in love with the place.  
Chuck brought her out of her observation, "Well as you can see I have a lovely home that you and your mother are welcomed to. There are more rooms just down that hall. I'll show you around here and the entire hotel tomorrow, but now I'm sure you're exhausted so let's get to bed."

The way he said 'let's get to bed' made her skin hot, she felt flushed but she just nodded. "I'll get my mother to bed, just show me her room."

Chuck turned to his right and pushed open the double doors. "This is where your mother will be staying, our room is right across the hall."

He smirked at her but despite the smarmy way he said 'our room' she was glad he put her mother right across the hall. "Thank you, I'll be right there in a minute."

Chuck nodded and turned to the room across from where they were. Blair guided her mother into the room and got her ready for bed.

"Goodnight mother."

"Goodnight dear, tell that nice young man I said goodnight too."

Blair smiled and laughed, "I will." She kissed Eleanor on the cheek and walked out of the room and shut the doors gently behind her.

Blair quickly took a deep breath before pushing the doors to her own room open, bracing herself for what she'd find behind them. What she did find wasn't what she expected. She expected to see Chuck naked waiting with handcuffs but what she found was Chuck sound asleep in bed. He was on the right side and left a lot of space for her.

She smiled to herself as she changed into the night-clothes she had brought with her. It was the nicest pair she had. She slid into bed next to Chuck and was unsure of how to sleep. She had the urge to be close to him but didn't want to make the first move. She was grateful for what he was doing but she knew he was only helping himself and a friend. There was no way such a powerful man could want her, she didn't feel sexy or beautiful like Serena.

She finally decided to give in to her urge and just move closer to him, so she moved up behind him and lightly put her arm under his. She was about to settle down to go to sleep when she felt him turn around. She gasped and sat up abruptly. "I I thought that that you were sleep, I'm sorry", she said as she looked down at her lap.

Chuck gently grabbed her chin and lifted it up to make her look at him. "Turn over", he commanded. She hesitantly did as he said. She turned over and laid back down feeling a little rejected. The feeling quickly went away as she felt his strong arms wrap tightly around her. He pulled her to his chest and laid a kiss on top of her head. "Get some sleep, you have a long day ahead of you tomorrow."

And they did, Blair slept pushed to Chuck's chest all night and they both had smiles on their faces. At a quarter to 5 Chuck awoke to the door of the bedroom opening. Chuck looked up to see Eleanor at the door. He didn't know what to do, but he didn't want to wake Blair up because she obviously needed the sleep if she dealt with this everyday. Chuck gently let go of Blair and got out of bed. He put his robe on and walked over to Eleanor. "Hello", Eleanor said. "I'm looking for the bathroom I can't seem to find it."

"It's right this way ma'am" Chuck said leading him to the bathroom in his room. He waited by the door until she was finished, then he lead her into the kitchen. "What would you like to eat?" Chuck asked her.

"What do you have?" Eleanor asked reminding Chuck of a small child.

"Anything you'd like."

Eleanor grinned widely, "I'd like french toast with maple syrup, scrambled eggs, and crispy bacon."

"Okay coming right up. What would you like to drink?"

"Orange juice."

"Orange juice it is."

Chuck dialed room service and ordered Eleanor's food and bagels and eggs for himself. Just as he hung up Blair walked out of the bedroom stretching and yawning. Chuck thought she looked so cute waking up, he could wake up to her every morning. The thought was foreign to him and it scared him. "Good Morning", he told her. "Sorry if we woke you."

"Good morning" Blair replied as she walked up to him and kissed him. She looked down at her feet feeling embarrassed. Chuck hid his shock and just chose to go along with it and hugged her. Blair looked up at him, "I usually wake up at this time to fix her breakfast."

"It was no problem at all, I ordered her breakfast" Chuck said looking at his watch. "I'm sorry but I'm running late I have to get ready for work. You should order something to eat for breakfast."

Chuck walked into the bedroom and began getting dressed. Blair walked in behind him. "I could help you get ready, I am your girlfriend after all", Blair smiled. "Thank you, could you go to my closet and pick out something for me to wear."

Chuck went into the bathroom and got into the shower. Blair walked into what she assumed was the closet. When she walked in she was floored, the room was huge. One side were filled with Chuck's things and everything looked expensive. The other side was bare, there was plenty of space for more of his things but she suspected that a woman's things belonged there. The side of the room where Chuck's things were had a masculine feel to it, his initials were carved on the mirror for the dressing table. The side that was bare had softer feminine features, the mirror and vanity was rounded and there were lavender touches on this side were as the other side was a deep purple. The gold accents on both sides bringing the two shades together nicely. Blair went over to Chuck's clothes and ran her hand over the suits looking at all the colors. She stopped at his grey suits and picked up a dark pinstripe for him to wear. She quickly put his outfit together and brought it to the bed just as he was walking out the bathroom.

Chuck had a towel wrapped around his waist and water was dripping down his body. He walked over the drawer on the right side of the bed and pulled out some boxers. Blair walked back in the closet to look at the bare side instead of looking at Chuck's bare side. "Why is this side of the closet different from the other?" Blair called from the closet. Chuck stepped into the closet and sat on the ottoman that was in there to put his shoes on. "My mother designed it for me and my future wife, and if I change it I'm sure she'd kill me", he answered with a shrug "Since you're staying her that side is yours to use."

"Really?" Blair asked excitedly, "but what am I going to fill all this space with?" Blair asked as she looked around the big room.

"Clothes of course, shoes, purses. By the time Raina gets done with you today I'm sure you'll be needed some of the space on my side."

"Who's Raina?" Blair asked looking down feeling a little jealous.

Chuck pulled her into a hug, "She's my personal stylist. Your going shopping with her today."

"Oh", Blair said looking down at his bow tie as she fixed it.

Chuck kissed her on the forehead. "Would you get my phone and call Raina and tell her to bring you to the salon for a make over also. Then tell her to bring you to John Pierre for lunch. I have to pack my briefcase for this board meeting today."

"Chuck I really couldn't, I won't have anyway to pay you back. I couldn't let you spend all that money on me just for an arrangement. You've already done enough for me and my mother."

"Blair just do as I say and we'll talk about how you can repay me later." Chuck went to kiss her again and Blair turned her head. She was hurt and disappointed. She didn't know why she expected him to actually care or like her, he was just helping a friend and himself she reminded herself. He expected to get sex out of the deal too.

Chuck looked at her and just kissed her cheek. He didn't know what he said to upset her so he just brushed it off. "Buy your mother some clothes and things too and bring her to lunch with us I would love to get to know more about her. Also you two and Dorota can go to the spa in the hotel and get whatever you want, just ask Raina where it is."

Blair just nodded and pulled his phone out of his hand as he turned and went back into the bedroom. She dialed Raina's number and relied the message from Chuck. Raina was nice and sounded like fun. Blair couldn't wait to meet her and spend the morning with her, Blair didn't have many friends besides Serena and this girl Hazel she worked with.

Blair had just gotten off the phone with Raina when Chuck's phone started to ring again. Without thinking Blair answered it. "Hello?" a woman's voice asked from the other line.

Blair looked at the screen to see that it was a woman named Eva. That name sounded familiar to Blair but she couldn't quite figure out where she know of this woman from. Eva called out again, "Hello?"

Blair answered this time, "Yes hello."

"Who is this?" Eva asked sounding irritated.

"This is Blair, may I ask who's calling?" Blair said smirking to herself. She knew that would make the woman mad.

"This is Chuck's girlfriend, who is this?!"

"Well you must be mistaken because it didn't seem like you were his girlfriend when he was bending me over last night and fucking me. He was screaming my name over and over, and I didn't hear him mention you once the whole night or this morning when I woke up to him eating my pussy. Are you sure you're his girlfriend?" Blair said with an innocent tone.

Chuck stood at the closet door looking amused. "That must have been some hell of a night, and a tasty breakfast", Chuck said with a smile walking over to Blair.

Blair gasped and spun toward him, her face turned beet red.

Eva was still on the phone, "What?! You slept over there? Where is Chuck, put him on the phone now you whore."

Blair instantly knew where she'd known Eva from. Her and Chuck were posted over all of the newspapers, she was a prostitute that Chuck was seeing. Blair not missing a beat, "Whore? You're the one he paid for sex, while I'm getting it for free. He and I are in a real relationship and you're just a tax write off! I sleep in his bed at night, in his arms after he makes love to me. You get dropped back off in the streets with the dogs and fleas after he gets off."

"I want to speak to Chuck!"

"Sorry he's busy right now, his mouth full of my pussy at the moment I'll have him call you back when he finishes me off." Blair smirked then hung up the phone.

Chuck looked at Blair and laughed, "You are an amazing little woman."

Blair just glared at him and handed him back his phone.

Chuck shook his head and laughed some more, "See you for lunch Blair." He went to kiss her and she turned her head again but this time

Chuck pulled her in close and grabbed her ass. Blair looked up at him and his face was so close. Chuck pushed his lips to hers and when she gasped he stuck his tongue right in. He began tongue kissing her and massaging her ass.

Her ass was firm but well-rounded, and her hips were perfect for him to grab on to. Blair was kissing him back and grabbing the hair at the back of his neck. She was getting so turned on, she forgot about why she was even mad earlier. Chuck finally pulled away, "I am really late for work but I am not complaining." He smiled and kissed her cheek before he grabbed his briefcase and ran out the closet.

"Have a good day at work!" Blair called after him. She smiled, this was defiantly a dream. Yesterday she was barely getting by working at a job she hated, and today was she in the penthouse of the Empire going on a shopping spree and to the salon and spa. By helping Serena and Chuck she was getting almost everything she ever wanted. Maybe if she were successful she'd find love, she only hoped so.

Chuck made his way into his office, his secretary Penelope was waiting for him. "You're late Mr. Bass, Mr. Archibald is waiting to see you. He just ran to get some coffee."

"Thank you Penelope" Chuck said as he sat down behind his desk. "Please clear my schedule for the day after the board meeting."

"Of course sir."

Penelope left his office just as Nate coming in.

"Where were you this morning buddy, you were late. Chuck Bass is never not in the office by 6. What's up man?"

Chuck got up and started pacing the room. "What's up is you have brought my death upon me."

"Woah what are you talking about man?" Nate asked clearly amused. He'd never seen Chuck this bothered.

"I'm talking about the 5'5 brunette you brought into my life. I hope you're happy."

Nate laughed, "What's up with Blair? Is she causing you trouble already?"

"Yes Nathaniel she is. She's causing this fluttering in my stomach that won't go away. She's making me do things I'd never do, I don't know what's wrong with me." Chuck put his head in his hands. "We cuddled, Chuck Bass doesn't cuddle. We didn't even fuck!"

"Chuck you like her, I don't see the problem. This is great, it makes the situation easier." Nate patted him on the back.

"Nathaniel you don't seem to see the seriousness of this situation. It's bad enough I suddenly have a girlfriend but to actually like the idea of it? That's crazy, I'm not a one woman man. What the hell is wrong with me?"

"Look man, chill. Nothing's wrong with having feelings, it just means you're normal. Blair's a nice girl, you shouldn't mess this up."

"She is a nice girl but she's still a woman. Women nag and try to control you. They want marriage and monogamy."

"What's wrong with monogamy?" Nate asked as he sat across from his friend.

"Why be with one woman when you can just hit it and quit it? Why put up with the nagging and arguing?"

"When you love someone they're all you need, they'll be all you think about so you wouldn't even want to be with anyone else. You put up with it because when it's over and things are good again you're the happiest you've ever been."

"Why do I get the feeling you're talking from experience Nathaniel? Something you want to tell me?"

Nate laughed a little then smiled, "I love her."

Chuck looked at his friend and for the first time noticed he had a glow. He seems genuinely happy. Chuck felt a little bit of envy, he wanted to be that happy. Maybe he should give dating Blair a serious try. He actually liked her and truly wanted to help her. She was fierce and didn't hold back with him. He liked that she told him exactly what she felt about him. She was bold and went for what she wanted. When she put her arm around him last night his whole body was on fire from her touch. He saw that he was loving and caring by the way she cared for her mother. She was determined and he loved that about her, but it also scared him.

If she ever put her mind to it, she'd have Chuck wrapped tightly around her finger. If she wanted a ring out of him, she'd have it. Chuck was deadly afraid of this woman who came in his life so abruptly but she intrigued him so much. She wanted to be powerful and he knew she could do it, he would help her get there but when she got to the top what would happen? He wondered if he would be able to handle the woman he was going to create. She had bitten already but with power she'd have a few bodies under her feet in no time. She'd been in his life for less than twenty-four hours and she already made Chuck Bass domestic.

Chuck thought about the woman who was in his bed last night and he smiled to himself. He was sure she'd be the death of Chuck Bass young rich playboy, would it be for the better or for the worst he didn't know yet but he knew for a fact he'd come out this thing a changed man nonetheless.

Chuck looked up at his friend, "Well my friend, I'm afraid you might not be the only one."

Nate looked at Chuck as if he'd grown two heads. "Blair must be one hell of a girl."

Just then there was a knock on the door, Penelope stuck her head in. "Mr. Bass the board members are ready for you in conference room 2."

Chuck stood up and turned to Nate, "Here goes nothing."

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**AN: Blair and Chuck will tell their back stories in the next chapter. I hope you guys enjoy, please review.**


	3. Hand Holding

**I do not own Gossip Girl or My Fair Lady.**

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Chuck straightened up his suit coat and walked to the conference room. He opened the door walked in with confidence, "Good morning ladies and gentlemen. Sorry I was a little late this morning."

Gary one of the older men snorted, "Yes I'm sure it was a rough night."

Mary shot a look at Gary, "Actually Charles that's what we wanted to talk to you about. Your ways are starting to make the company look bad. Christian and family groups are beginning to boycott. Your little friend Eva is threatening to go to the papers with her story of your dirty ways if we don't pay her $10 million dollars. This has got to stop!"

Everyone in the room looked at Chuck and nodded.

Chuck exhaled and thought back to the conversation he'd hear between Blair and Eva this morning, he was sure that Eva wouldn't be a problem with Blair in the picture now. "I assure that Eva will not be a problem now or ever again. I am aware of how my actions have affected the company, and I am deeply sorry." Chuck decided to go in for the kill, he knew just want to say to get the men's sympathy and the women's approval. "My girlfriend is making sure I pay severely for my actions."

Chuck had to hold back a smile as the board members all gasped. John who was not that much older than Chuck spoke up, "Girlfriend? Since when do you have a girlfriend?"

"She just came into my life suddenly and took me by storm", Chuck said with a sincere smile. It wasn't a lie.

Mary spoke again, "And who does your girlfriend feel about your indiscretions?"

"Well like I said I'm paying for it, as a matter of fact I'm sure she's getting ready to spend to go get a new wardrobe on me and I'm due to meet her for lunch this afternoon."

Just on cue everyone's phone beeped, it was the spectator.

**There's a mystery woman walking out of the Empire and getting into Chuck Bass' limo. My sources say she arrived last night with the playboy last night but she never left. We all know Chuck Bass' rule about girls spending the night, so why is this girl so special? Could she be close to the heart we never knew Chuck Bass had?**  
**-The Spectator**

Everyone looked up at Chuck, he smiled sheepishly then shrugged. "Well as you can see she's already starting her day so I'd say we start this meeting so I can be out of here by lunch time. I wouldn't want to make Blair even more upset."

The women smiled and the men said their sorries. "She sounds like one hell of a woman, I'd like to meet her", Mary said.

"That she is Mary, you'll meet her soon I promise", Chuck replied and then the meeting began.

Blair had just gotten dress when Dorota walked through the elevator with a man dressed in an Empire uniform. He nodded at Blair and Dorota before the elevator shut. Dorota walked over to Blair and hugged her, "This is nice Miss Blair!"

"I know Dorota, this place is lovely. I hope my home will be just as nice when I get my own."

Dorota looked confused, "This isn't your home?"

Blair looked away from her, "Yes for the time being, sort of..."

"Miss Blair what going on?"

Blair sighed, she knew Dorota wasn't going to give up. "Fine Dorota, this is Chuck's home. He's letting me and mother stay here for the time being while I help him."

"Help him do what exactly?" Dorota asked skeptically.

"I'm helping him with his business."

"And what do you get out of this?"

"I get to live her and I get to go to Yale", Blair smiled brightly.

"That is wonderful Miss Blair, I know you always want to go to Yale since you were little girl and be big successful woman like Miss Eleanor talk about."

"Yes and now that's going to all happen being of Chuck." Blair smiled when she said Chuck's name and Dorota smiled knowingly.

"You like Mister Chuck." Blair walked into Eleanor's room where the woman was sleeping.

Blair turned to Dorota who had followed her, "I do not! We are just helping two friends be able to be together and helping each other all in the process, it's all harmless. Besides I can't be a powerful successful business woman and let a man into my heart."

"Why not? You and Mister Chuck could have real relationship and everything work out."

"Chuck doesn't do girlfriends."

"I'd agree with you if he didn't have me come here on my day off to take you around the city and spoil you." Raina Thorpe said. Blair and Dorota were too busy talking to hear the elevator ding. "Hey I'm Raina, Chuck's personal stylist. You will be spending the day with me and Chuck's black card, which is my best friend." Raina laughed and extended her hand for Blair to shake.

Blair smiled at the beautiful woman in front of her. "Hello, I'm Blair Chuck's..."

"Girlfriend", Dorota added with a forceful look at Blair.

"Chuck already explained everything to me and I assure you that he likes you Blair, no matter what he may say. The fact that you've gotten Chuck to give me his black card would mean you mean something to him. He only gives me this card when it's something for Evelyn."

Blair was happy until she heard Evelyn and the fact that she got the black card too meant that Blair wasn't the only one Chuck had feelings for. She hid her disappointment and smiled at Raina, "Well let's be on our way."

Blair turned to Dorota, "Chuck said everything was on him and suggested the spa, take mother and enjoy yourself."

Dorota smiled and nodded. Blair turned and followed Raina into the elevator, and out the hotel. As Blair was stepping into the limo a boy came up to her and snapped a picture. Blair stopped confused, Raina looked at her questionably then she realized why Blair stopped. "It's okay, he works for Nate at the Spectator."

"Oh", Blair said simply and got in the limo. "So where to first?"

"The salon, I'm in need of a touch up."

The arrived at the salon and was greeted with sparkling water and macarons. Blair eyes lit up when she saw the macarons and she quickly grabbed one. She bit into it and felt she was in heaven.

"I see you like macarons," Raina said with a smile.

"Yes, they are delicious."

"Well we could have some delivered to the suite for later."

"Thank you, I would love that."

"Don't thank me, thank your boyfriend. You can have anything you could ever want and won't have to pay for any of it."

Blair thought about that and about all she wanted. She doubted she'd get real love, she wanted to be powerful and she couldn't have both.  
Blair sat down in the big chair and relaxed as the hair stylist did her hair. When she was done Blair couldn't help but smile looking in the mirror.

Her hair was shinier and smoother. Her curls had more volume and didn't hang limply down her back anymore.  
Raina came up behind Blair, "Your hair looks amazing, Zara did a great job. I grabbed the shampoo and conditioner she used for you to take home and set an appointment for you to come back in the next two weeks. Now let's go get your makeup done."

Blair sat in the chair of the make up salon as the woman did her face. Raina was on the phone with Chuck. When she came back in she had a huge smile on her face.

Blair looked at her curiously, "What are you smiling about?"

"No nothing let's go."

Blair picked up the bag the make up artist filled with make up for her to use at home.

Blair stood in the middle of the dressing room while Raina looked at her smiling. "That is perfect, Chuck won't know what hit him."

"I can't where this! It's too short."

Raina rolled her eyes, "Blair you're getting it. So take it off and add it to the rest of the things and let's check out so we can move on to lingerie."

"Lingerie?! I am not wearing or buying any lingerie."

"Yes you are."

They got up to the register and the cashier looked at the men carrying the mountains of clothes. The workers who were tasked to carry around the many clothes Blair picked out for her mother and herself, put the clothes down to be rung up.

Raina looked at all the clothes like they were nothing, "You have great taste, you should go into the fashion business."

Blair smiled proudly, "Thank you. I would love to go into the fashion business if I ever got the chance to."

As the woman rang up the clothes Blair looked at the amount, "That's too much, let's put some stuff back-"

Raina ignored her and handed the cashier Chuck's card, "Here you go."

"Chuck is not going to spend three million dollars for a stupid deal!"

"You obviously don't know Chuck, and please relax. Three million is pocket change to Chuck Bass. He told me to get you and your mother the best of everything, money is no problem."

Blair didn't reply but she still felt uneasy about the whole situation.

Blair let Raina drag her to La Perla's, Blair was bright red the whole time. "I don't see why I must have lingerie."

"Chuck likes lingerie, it's one of his weakness."

"Who says Chuck wants to see me in lingerie anyway, we aren't really dating."

Raina just ignored Blair and kept adding things to the pile, "Right... Here try this on."

"Why is there so much white?"

"Chuck has a fetish for the virginal thing, I think it's because he's like the devil."

Blair got even redder and looked down.

Raina looked at her suspiciously, "You couldn't be a virgin... Oh my God you are!"

Blair glared at her, "So what that I am!"

Raina scoffed, "How old are you exactly?"

"I am 19 thank you very much."

"And you've never had sex? Wow, we need to get you laid."

"I do not need to get laid!"

"You do, and we're going to handle that right now. You're going to wear this", Raina said picking up a white lace thong and lace slip. "tonight and nothing else tonight to bed."

"Why would I do that?!"

"Because Chuck won't be able to keep his hands off you I promise."

"We aren't even dating so why would I lose my virginity to him?"

"Because you like him and he likes you, you two just can't see it yet but you're defiantly dating. The deal before hand is just a good bonus."

Blair thought about it, "I can't wear this..."

"You can and you will, you'll look sexy in this trust me. You're going to have New York's most eligible bachelor in the palm of your hand by tomorrow morning, I promise."

"How do I know if he even likes me? He's Chuck Bass, he doesn't do girlfriends."

"The fact that you know of me is a good indication that he likes you. I work for him, none of the girls he's been with knows his employees. He's using his black card for you but if you still aren't convinced you'll know he likes you if he lets you hold his hand. Evelyn is the only person that's ever held Chuck's hand."

"We'll see..."

"No way am I doing this!" Blair screamed. She was currently laying on a table in a spa that Raina said "gave the best waxes".

"Blair you want your first time to be magical, so we don't need any hair down there. Now shut up and let the lady do her job."

Raina turned to the lady with the waxing strips, "Brazilian."

"I am not losing my virginity to Chuck Bass, who is my fake boyfriend."

Raina sighed, "For the last time Blair, he likes you. I'd even say he more than likes you because he's doing things he's never even thought about doing before. You're the first girl to ever sleep in Chuck's bed, and he's taking you and your mother out on a dinner date. Chuck Bass didn't do dates, but he's doing them now so shut up and enjoy all that Chuck Bass has to offer. Now I'm going to go over here and get you some shower gels, bath oils, bubble bath, lotion, and perfume. What scent do you like?"

Blair gave in, "Vanilla Musk."

"Perfect."

Blair thought about what she said. If he did actually like her what would be so bad about losing her virginity to him? Blair liked Chuck but she didn't know how he felt about her. He did insult her when they first met but Blair knew that was all a front. From what she'd seen of Chuck Bass so far he was kind and a very caring person but not many people knew that. He was a guarded person but once he let you in you could see how he cared for those he loved. The man she laid in bed with last night wasn't a womanizer, he was the perfect gentleman. Chuck was a powerful man and that turned her on, she just didn't know if he felt the same way about her. She wanted a true relationship with the man she'd slept beside last night, the one that got up and helped her mother. She didn't want it to just be about the bet, she wanted to start something real and see where it went. She just didn't know if Chuck wanted the same, and she didn't want to seem weak. She didn't want to be vulnerable if she fell in love, she wanted to be powerful. Blair grew up thinking love made a person weak, that's why she'd never lost her virginity but she wanted to see where this could go. Blair wanted to give her and Chuck a try, she didn't have to fall in love right?

They went back to the hotel to pick up Eleanor and drop off all the bags.

"Bring all the bags up to Chuck's suite and put it in his closet", Raina told an employee.

"Yes ma'am."

Eleanor was coming out the hotel behind Dorota. Dorota was smiling, "Miss Eleanor was wonderful today. She really like it here."

Blair smiled, "I'm glad."

Eleanor looked at the men carrying all the bags, "Oh my, who are all these bags for?"

"They're for us."

Eleanor smiled and got into the limo just as the last bag was being brought into the hotel.

"Where are we going?"

"We are going to lunch with Chuck."

"Who's Chuck?" Eleanor asked confused.

"He's my boyfriend."

"Oh that's wonderful dear, I can't wait to meet him."

Raina came to the door of the limo, "I'm going to get going, Arthur knows where to go. I had fun shopping with you today, if you need anyone to talk to give me a call and remember what I said about tonight!"

Blair blushed and waved, "Bye."

Raina shut the door and they were off to John Pierre. When they arrived Chuck was sitting on the patio of the restaurant nestling a drink. Blair grabbed her mother's arm and led her to where Chuck was sitting. When he saw them he stood and greeted them. "Hello", he said as he kissed Eleanor's cheek and then kissed Blair on the lips.

Eleanor just smiled at the two and sat down. Blair and Chuck followed her and the waiter approached. "Can I get you ladies anything to drink?"

Blair looked at the menu, "I'd like the green tea please." She turned to her mother, "What would you like mother?"

"I just would like water."

The waiter nodded, "I'll be back shortly with your drinks and to take your orders. Sir can I refresh your scotch?"

"No thank you, just bring me some water also."

"Of course Mr. Bass."

The waiter turned and left.

Chuck looked towards Blair, "So how was your day of shopping and how much did it cost me? I'm sure Raina was a delight."

"I had a great time with Raina, I'd like to meet up with her again. We spent about 3 million, but I'm going to find a way to pay you back-"

Chuck put his hand up to stop her, "Blair it's fine really, you don't have to pay me back. Three million isn't much to me, I thought you would've spent more. Although if you'd like to pay me back-"

"If you want sex for the things I'll just get a job and pay you back really."

"I was going to say you could accompany me on a date, but I guess not", Chuck said with his jaw set.

"Oh", Blair said looking down at her lap. "I'm sorry."

"It's fine", Chuck sighed.

There was an awkward silence until the waiter came back with the drinks.

"Are you ready to order?"

Chuck spoke first, "Yes I'd like the classic French toasted ham and cheese sandwich with a green salad."

"I'd like the lobster bisque", Blair said. She then turned to Eleanor, "Mother what would you like?"

"I'll take whatever you're having dear."

The waiter wrote down their orders, "Your meals will be ready in a moment."

Chuck nodded then turned to Blair, "Look I know this may be difficult for you to adjust to but I'm trying. Let's just get to know each other, you seem like a nice person to know and I would love to really know you." He picked up Blair's hand and held it in his.

Blair gasped and smiled remembering what Raina said. Chuck looked at their hands and quickly dropped her hand and cleared his throat. "I'm sorry", he said.

Blair grabbed his hand, "It's okay Chuck. You don't have to hide who you are from me. I want to get to know you too." She smiled at him.

Chuck looked down at their hands, "I've never done this before, I don't feel like myself. For once in my life I don't know what to do and it scares me." He looked up at her.

"It's okay Chuck, I feel the same way and it scares me too but I don't want to be a coward and run away from it."

"Blair when I first saw you I thought you were beautiful, and I've never thought that about any other woman but my mother. Last night I was content with just holding you, and when you woke up I had this thought of you waking up to me every morning."

Blair was about to ask him a question when the waiter came with their food. He sat the food down then excused himself. They fell into a comfortable silence for a while until Blair spoke. "Chuck can I ask you a question and get a serious answer?"

"Of course, I'm usually always honest", Chuck said with a smirk.

Blair rolled her eyes then had a serious face, "Chuck how do you feel about me?"

He exhaled deeply, "Well honestly Blair I like what I see and know so far. I would love to know more about you though."

Blair smiled, "Well what would you like to know?"

"Everything."

"Well how about I tell you the basics and then we talk more intimately over dinner tonight?"

"That sounds wonderful, where would you like to go?"

"I was thinking we eat in."

"Whatever you'd like Blair", Chuck said as he brought her hand up to his lips and kissed it.

"Okay, so ask me some questions and whatever you ask me I will ask you back and you have to answer. Deal?"

"Deal. First what is your full name."

Blair laughed, "Blair Cornelia Waldorf, you?"

"You should already know, but it's Charles Bartholomew Bass. What is your mother and father's name?"

"Eleanor and Harold Waldorf. You?"

"Evelyn and Bartholomew Bass-"

"Wait! What is your mother's name?"

Chuck looked confused, "Evelyn, why?"

Blair was embarrassed, she turned bright red. This whole time when Raina would mention Evelyn she would feel disappointed and jealous, when she really had nothing to worry about. "Oh no reason."

Chuck didn't look convinced but he dropped it. "Right..."

"Next question."

"Okay how old are you?"

"I'm 19, you?"

"25. What's your favorite color?"

"Blue. Yours?"

"Purple. Why aren't you already in college?"

"That's not a basic question."

"Well I couldn't help myself", he said as he looked at his watch. "We've been here a while, how about we take your mother to a museum. Eleanor must be bored."

Blair smiled at him using the information he'd learned. Eleanor turned her head towards Chuck. "Yes?"

"I was going to ask you if you'd like to go to a museum?"

"Why yes, I would love that." Eleanor smiled.

"Okay let's get out of here."

Chuck paid the check and escorted Blair and Eleanor into the limo that was awaiting them.

They drove to the Metropolitan Museum of Art. Chuck helped Blair and Eleanor out of the limo and they walked up the stairs. Eleanor stopped and looked at every piece, she was really enjoying herself. Blair smiled seeing her mother so happy, and before she knew it she felt someone grab hold of her hand. She looked down and noticed it was Chuck's hand, she was shocked. He was holding her hand as he talked to her mother about the pieces and guided them through the museum.

* * *

**I know I said their background stories would be in this chapter but it was too long. They will get to know each other better over a nice romantic dinner.**


	4. The Look

**I do not own Gossip Girl.**

* * *

They walked around the museum laughing at Eleanor until she got tired, then they went home. When they got home Blair put Eleanor to bed. She went across the hall to her and Chuck's bedroom, where he was standing at the entrance of the closet.

"This isn't much, you must go shopping again. Although I do think I'll like what's in the La Perla bag. Present for me?" Chuck said without turning around.

Blair walked over to him and put her arms around his waist, "Maybe, if you're a good boy."

He stepped out of her arms and brought her to face him and pulled her into his arms. "I'm always a good boy, well as good as I'll ever be. I am Chuck Bass after all."

"And I'm Blair Waldorf, so you should be a good little boy and go play while I unpack this stuff. If you're good there might be a special treat for you before bed."

Chuck's eyes darkened, "You really shouldn't tease me Blair, a hungry Bass is one hell of a problem to deal with. And I'm far from little, I'm a big Bass." He smirked and kissed her. "I'll be in my office working until dinner, but if you need anything at all just call staff they're at your beck and call."

Blair smiled at that, she was use of waiting on someone not someone waiting on her. It feel so nice, she felt like this was the start of her reign. Blair was determined to conquer Manhattan and be its Queen but first she was going to bring down its dark knight and make him her King. Blair knew that she could do it, she'd changed him without even trying so she knew she could make him fall in love with her. With Chuck Bass as her King she would be a force to be reckoned with. She was just afraid that she'd fall for him back and that would weaken her. She wanted to be established and on top before she fell in love.

Blair looked at all the bags and decided she needed help. Blair went back to the bedroom in search of Chuck's phone, she would have to tell Chuck to get her one tomorrow since hers had been broken and she didn't have any extra money to get it fixed or get a new one. When she found the Blackberry on the nightstand on his side of the bed she went to pick it up. As soon as she picked it up to dial Serena's number it started to ring.

Blair looked to see who was calling and gasped, it was Evelyn Bass. Blair knew she couldn't answer it, so she went to put it down and accidentally pressed the talk button. Blair eyes got wide as she saw the timer counting down, indicating that the call was connected.

"Chuck dear?" Blair heard Evelyn said on the other line.

Blair took a deep breath and slowly picked up the phone, "Hello?"

Evelyn was silent for a minute, "Hello, who is this?"

"I'm Blair, a friend of Chuck's. I'm sorry I was going to use his phone and I accidentally hit the talk button, I'll put him on the phone right away."

Evelyn ignored her, "Blair is it, you wouldn't by any chance be the girl who happened to be in the Spectator would you?"

"Umm yes ma'am I am."

"So it's true, my son finally got himself a girlfriend?"

Blair thought about it for a minute, he did say he like her and they were doing boyfriend and girlfriend things but if they weren't really dating she didn't want to seem like a liar to his mother. "It's complicated."

Evelyn laughed, "Honey most things with a Bass man is but since you're obviously in his bedroom alone you mean something to my son.

Where is he?"

"He in his office working ma'am."

"Please call me Evelyn. Could you tell my son I'm coming over right away, and don't you go anywhere I want to meet you."

Before Blair could reply Evelyn hung up. Blair sat the phone back down and got up to go tell Chuck of the arrival of his mother. She was sure he was going to be angry and it made her nervous to think of what he'd do to her once he found out she'd answered his mother's call. He'd been so kind and generous to her, but after this he'd probably make her and her mother move somewhere else and make her work again.  
Blair lifted her head high and walked down the hall in search of his office. She was prepared for whatever he was going to do, she'd still reach her goals no matter what set backs Chuck Bass presented to her. After opening three doors in the hall, she finally opened the door to Chuck's office.

He was sitting at the big brown desk swirling what looked like scotch around in a glass tumbler and staring intently at some papers. Blair knocked to let her presence be known. Chuck looked up at her, he could tell she was nervous but was trying to hide it.

"Blair done so soon?" He said with a smile.

Blair walked over to him and stood beside his chair, "Not quite, there's something I have to tell you.."

"What is it?" Chuck asked confused, not sure what she would've possibly did wrong in such short amount of time.

"Well your mother's on her way over because I accidentally answered your phone", she rushed out.

Chuck was silent so she continued, "I'm sorry Chuck I was going to call Serena because my phone is broken and I need help putting everything away-"

Chuck put his hand up to stop her then motioned for her to come to him. She stepped closer and he pushed his chair back from the desk and pulled her into his lap. "Blair it's fine, really. You were bound to meet my mother sometime and I promise you she'll love you."

"You aren't mad I answered your phone?"

"I don't care if you answer my phone, you've done it before. I'm not trying to hide you from anyone and I'm not trying to hide anyone or anything from you, but you should get another phone so you can have something to use while I'm at work. You can order one today, my card is in my wallet inside my nightstand. I'll be getting you a card and setting up a bank account for you tomorrow."

"You're really going to do that for me? Chuck that's too much, you couldn't possible do that for a stranger."

Blair thought about where this was going, she wanted him to fall in love with her but if that put his empire in jeopardy she couldn't do it. She needed him to be powerful so she'd have a powerful man behind her.

"Blair you're my girlfriend, this isn't a game to me anymore. I like you, and you like me too."

"You aren't afraid though?" Blair asked looking down at her lap.

"Honestly yes, I'm afraid to let you in but I'm going to try."

"You afraid that I'll make you weak?"

"Weak? What do you mean?"

"Love makes you weak Chuck, I don't want to fall in love with you and be weak and I wouldn't want that for you either. I want her both to take over Manhattan, we can't show weakness."

Chuck laughed and Blair scowled at him, "Blair you can't help that we're falling for one another, just go with it." He rubbed his hands up and down her side "We won't be weak just because we show weakness with each other. I've learned that you can't be strong all the time it wore you out. When we're alone I'll show you how to let go and when we're among people I will show you how to crush the competition and control the masses."  
Blair was getting turned on by this talk of power and control, she kissed him deeply and straddled him. Chuck was running his hands up her dress and grabbed her ass roughly when he felt that she had on a thong that covered nothing. Blair yelped and grabbed at his hair, he began kissing and licking at her neck. She grinded on his dick which was rock hard and he palmed her breast through her dress. Someone at the door cleared their throat and the two separated quickly.

Evelyn Bass was standing at the door with her hand on her hip looking very amused. "Well hello Charles, Blair."

Blair tried to stand but Chuck held her down, she glared at him and he glared back. Blair quickly realized that he was hard and didn't want Evelyn to see. Blair pulled his hands from her and walked swiftly over to the door and ushered Evelyn out of the office before she could see Chuck and his condition. "Hello Evelyn, I'm so happy to finally be meeting you. I've heard so many good things about you, come let's go sit on the terrace and have tea", Chuck heard Blair say as she and his mother walked up the hallway.

Chuck exhaled and ran his hands over his face. He sat back in his chair and thought about what she'd said about being weak. He'd heard that love would make you weak all his life, it was his father's motto. His father never showed love and he was successful at everything, except being a good father and husband. Chuck never wanted to be like his father, he wanted to be better. Bart Bass was a cold-hard business man. He had been in love with Evelyn when he had nothing, then he became big bad Bart and he turned cold. He married Evelyn for the family man look but he was anything but that, he had mistresses and never came to anything Chuck did. He missed anniversaries, birthdays, and holidays when they weren't being photographed or interviewed.

Evelyn played her part well even though she knew about the mistresses, but she stayed to secure her and Chuck's lifestyle. She knew if they divorced he'd get the best lawyers to make sure she didn't get a dime and she'd cut off Chuck's trust fund, then make up a story about how she was a cheater and Chuck was on drug and out of control.

Chuck loved his father once upon a time, before he grew up and realized what was really going on. He saw the pain his mother was going through and he never wanted to be like his father. He needed to be better, but he found himself living in his father's shadows daily. He decided then and there that he would have it all, he was be a powerful man and have a loving family.

He got up and walked on to the terrace where his mother, Blair and Eleanor were laughing. Blair looked up and him and smiled and he thought his heart had stop. She was beautiful with the wind blowing her curls lightly and the sun shining on her making her seem to glow. Evelyn looked at her son and gasped, he looked down at her with his eyebrows drawn together. Evelyn just have him a knowing smile, her son was in love.

"Charles Blair was just telling Eleanor and me how you two meet, and it's a rather amusing story."

Chuck blushed and looked at Blair, "You told them the whole story?"

Blair looked down at her tea, "The whole story."

Chuck rolled his eyes, "Well I'm going to go back and finish my work so I can join my lovely girlfriend for dinner tonight and you three can continue gossiping about me." He bowed then turned to leave the three women who were in my life as of lately.

"Now that he's gone back to work why don't we discuss your relationship with Charles" Evelyn said with a smile.

Blair blushed and looked down, "I don't know what you mean."

"You and my son are in love any mother can see that", Eleanor nodded in agreement and Blair smiled at her mother who was back to her normal self for a moment. "The way you two met is very Bass like."

Blair turned to Evelyn, "How so?"

Evelyn smiled at the memory, "Well Charles' father, Bart, and I grew up together. I was dating his best friend who we'd both known since diapers. I hated Bart, he use to always torment me and I him. He was the bad boy and I was the Queen of Manhattan", she laughed. "It was just before my 17th birthday when my boyfriend and I got into a fight. I went to Bart to forget and after only a couple sips of champagne I had got daring and I danced for him. The way he looked at me made me feel alive and desired. He was giving me a ride home when I'd kissed him, and he asked me if I was sure. I was a virgin but I was sure that I wanted Bart at that moment, I felt something strong between us. So right there in the back of his car we made love."

Blair and Eleanor were speechless. Blair knew the look she was talking about, she wanted to see it in Chuck. She'd seen in on her mother once before her father had left them. She'd seen it on her best friend and Nate. She didn't see it on Evelyn's face at the moment though and she wondered what happened.

Eleanor broke up the silence, "So Evelyn is it?"

Evelyn smiled softly and nodded her head, "Yes."

"What is it that you do?"

"I'm an interior decorator."

"Chuck told me you decorated his closet", Blair added.

"Yes his closet, and this whole hotel. This penthouse included."

Blair gasped, she was in awe. "You must have made a lot of money."

Evelyn shrugged, "Well when Bart died and left Charles the company, I put my degree to use and opened my own interior decorating company and I work with Bass Industries and a few private companies. I also work with some homes but I like to work with bigger space."

"So you made your own money?" Blair asked.

"Well not quite, when Bart made his first million I started a secret savings account and Bart put me through school."

Blair thought about that, Chuck was putting her through school and he was giving her money. She knew that a secret savings account would be smart to have. She wanted to own her own business like Evelyn Bass, she wanted to have a powerful man on her side like Evelyn.

Maybe love didn't make you weak but it had for Eleanor though, she loved Harold and he'd used her and left. Blair saw her mother's designs and knew she would've been a famous designer but she wasn't because she put her life on hold for the man she loved. Harold wanted to be a successful lawyer, so he went to school while Eleanor stood home and worked as a seamstress and took care of the child he'd wanted to have. When Blair was old enough to go to elementary Eleanor had to work two jobs to put her into a good private school.

Harold finally finished school and got a job at a top firm because Eleanor made dresses for one of the partner's wife. Harold quickly became a success and became a partner. When Blair started middle school she walked in on her farther with one of her mother's clients. Harold told Eleanor he was leaving her that night and left her with nothing. He didn't even say goodbye to his daughter. Blair hadn't heard from her father since then, but she knew he was rich and successful.

She never asked him for anything, even when Eleanor became sick when Blair was 16 and needed a nurse. Blair found a job and began taking care of the bills, her mother, and going to school. Blair was the valedictorian and would have easily made it into Yale if she had the money to go. She also did want to leave Eleanor. She just wanted to become a powerful and successful woman so she could take care of her mother and neither of them would have to work as hard as they did.

Blair wanted to have it all but she didn't believe it were possible, if her mother hadn't love Harold she would've never had Blair and would've been working to make her business a success.

"How did you become successful with a husband and a child?" Blair asked Evelyn.

"Well Blair I don't know how much you know about my late husband Bart but he wasn't much of a husband or father."

Blair frowned at this, maybe she really couldn't have it all.

Evelyn smiled a sad smile, "I know what you're thinking and you're wrong."

Blair just looked down. Eleanor who was quiet seemed to be dozing off.

"Why don't we take her in and I'll sure you the whole house if you haven't already seen it?" Evelyn offered.

Blair nodded and they brought the sleepy Eleanor to her room.

Evelyn showed Blair where everything was and Blair was amazed, Evelyn had decorated the home beautifully. When they were finished the tour they ended up back in Chuck's bedroom.

"So I assume you sleep here with Charles since none of the other guest rooms are untouched and I see shopping bags in the closet."

Blair blushed and Evelyn laughed, "Dear you mustn't be shy around me. My son never is and I've grown use to his indecencies after his third lost weekend."

"Lost weekend?" Blair looked confused.

"Every year Chuck and his friends have a party where they indulge in excessive amounts of drugs, alcohol, and women." Blair frowned and Evelyn shrugged.

"Please Evelyn tell me all about Chuck."

Evelyn smirked, "It'll be my pleasure. I'll tell you all the embarrassing stories while I help you put your things away."

"Thank you, it would have taken me days to put all this away." Evelyn nodded.

Blair looked down at the floor, "How do you put up with all the women? I've been here for just about a day and I've already had to deal with Eva the parisian prostitute."

Evelyn laughed, "Blair Charles is a Bass man, and Bass men attract women to them but they aren't all bad. With Bart I dealt with it by putting my time, energy, and love into Charles and not that he's grown up I have my business. And I'm sure you could put any of those woman in their place, I always went for the route of ruining their lives. But I know you are afraid to fall in love with my son, tell me why."

Blair looked at Evelyn and broke down, she told her the story of her father and how she's had to work hard to get by. She sobbed into Evelyn's arms and Evelyn rocked and comforted her.

"Shhh, it's okay Blair. I know how your mother felt. Bart didn't leave me but he wasn't there for Charles are me, he had many affairs and was hardly ever there for us but we made it through. I believe if your mother hadn't gotten sick she would've been a highly successful designer. You can make her proud Blair, go to school and become exactly what you want to be. You have Charles here for you and me too, you can use all of our resources and connections. I know my son and he's going to take care of you now, and that won't make you weak. I use to feel that way but then a special man came into my life. I was afraid I'd have to take the backseat to a man once again but instead of me being behind him he stood beside me through everything. I'm successful on my own but when I'm with him I'm successful and happy", Evelyn and Blair laughed. "If my son makes you happy, let him."

She continued, "He's not like his father or yours. The only things he got from the Bass' is the Bass man's charm, temper, determination, and ability to please women. Everything else is me, he's kind and loving although he'd deny it in front of everyone else. He despises his father, he never wants to be anything like Bart. Once he's with someone he won't cheat, so if you want my son to be loyal lock him down." Evelyn laughed and Blair smiled and nodded.

Blair and Evelyn were sitting on the floor of the huge closet laughing hours later. Chuck stood at the entrance to the closet smirking, "Please tell me you aren't telling her about the time I got drunk and mooned the Bass family for Christmas?"

"That was about 20 minutes ago dear", Evelyn told her son.

"Well mother now that you've embarrassed me I think it's time for you to go home."

"Chuck! You can't kick your mother out! We are talking", Blair huffed at him.

"Our date is in an hour you need to start getting ready and so do I."

"Blair dear it's alright, he's been kicking me out ever since he had hit puberty and I should be getting home. I have to get ready for Jack's arrival tomorrow", Evelyn smirked while Chuck cringed.

Blair looked curious, "Who's Jack?"

"My fiancé", Evelyn answered with that look in her eyes that had been there earlier when she told Blair about the man she was with.

"My uncle", Chuck said pointedly at Evelyn but then saw the look in her eyes she always had when she thought of Jack. "but you can't help who you love." Chuck smiled.

Blair smiled at the two, she could see that Chuck loved his mother so much and Evelyn obviously loved her son. Blair looked up at Chuck who was smiling at his mother and her heart-felt like it stopped. He was beautiful smiling and looking carefree. The lighting of the closet shone brightly on him and his hair seemed almost black and she could see the love shining from his eyes. She wanted him to look at her that way someday.

Evelyn looked toward Blair and saw the look that her son had earlier being directed towards him. She got up and smiled, "Well I'll be going, but Blair I understand you two have a date tonight so why don't you let me take Eleanor for the night? I have plenty of room and I'm going to be lonely until Jack gets here tomorrow. I'm sure she could use a girls night."

Blair smiled, "Yes, I would appreciate that and I know my mother would love that."

Evelyn smiled and nodded. She picked up the some of the bags with Eleanor's clothes. "I'll have her back tomorrow before lunch, if we aren't having too much fun."

Evelyn went to Eleanor's room and packed some of her things into a suitcase of Chuck's while Blair skipped to the bathroom to get ready for the night. When Evelyn was done Chuck walked the two women to the elevator.

"This is going to be fun", Eleanor said with a smile quietly more to herself than the others. Chuck smiled at her.

"Thank you mother, I know this means a lot to Blair", Chuck told his mother when they were near the elevator.

"No problem, just have fun tonight and don't mess this up! I like her, I want a daughter -in law and a grand child soon."

"Me too", Eleanor who Chuck didn't know was even listening added as the elevator's doors closed. He heard Evelyn and Eleanor laugh and he stood there shocked.

* * *

**I am updating as fast as I can and trying to make the plot flow as best as I can, I'm glad you all like the story though. I saw My Fair Lady and fell in love with Professor Higgins and Eliza Dolittle. The ending was my favorite part. There will probably be smut the next chapter.**


	5. First Time

**I do not own Gossip Girl.**

* * *

Blair got out the shower and headed into the bedroom looking to see where Chuck was. She saw that their room was empty so she quickly went into the closet and got changed into the dress that Raina insisted she got. It was black and backless, the neckline was plunged low enough to show cleavage but now a lot. It was very scandalous and something she didn't usually wear but she wanted to impress Chuck and have him under her spell.

She was going to seduce him tonight and thank him properly for all he's done. She went to the vanity and styled her hair into a simple up do and then did her makeup light. She walked out of the room and noticed he wasn't in the living room or kitchen either. She figured he was getting ready in one of the other rooms. She walked up to the phone that was in the living room and dialed room service. She ordered their meal with some champagne. She wasn't sure what kind to get because she never had champagne before so she just chose the first one the man suggested.

When she was done ordering the food she went to the kitchen to get some candles which she knew the playboy had. She was right, it was in a cabinet in the kitchen. She laughed and went to light them with the lighter that was with it and put them on the table. She walked over to the entertainment system and put on some of the music he had and turned it on low. Lastly she dimmed the lights until they were almost off just as the elevator dinged alerting her of the arriving meal.

The servicer was surprised to see the intimate a romantic setting, usually when room service was called at this time of night it was for strawberries, chocolate and whipped cream. He smiled at Blair and wheeled the meal and champagne in and prepared the table for her. When he was done she was heading out but Blair stopped him.

He was such a big help and she would feel bad if she didn't give her a tip. She once was a worker that lived off tips herself, so she felt the need to help others now that she could. She however didn't have any money so she told him to wait right there. Blair went in search for Chuck everywhere but he was nowhere to be found so she went to their bedroom and looked through his nightstand. She was shocked at all the things she found but just shook her head and continued in search for some money.

She couldn't find any so she went back to the living room. Chuck had just walked through the elevator doors and sat shocked at what he saw.

"Wow Blair, all this for me? I feel so loved", he joked lightly.

Blair just rolled her eyes, "Chuck give the man a tip."

Chuck looked at the server and the man looked down at his feet. He raised an eyebrow but just put the boxes in his hands down on the counter then reached in his pants for his wallet. He pulled a crisp hundred-dollar bill and handed it to the man. The man and Blair were shocked. The man quickly said his thank yous and leave with a bow.

"That was a hundred dollars", Blair said stunned.

"Yes, that's usually what I tip people."

Blair just looked at him with wide eyes, she never really imagined just how rich Chuck was until then. If he gave a hundred dollars away as a tip just how much was in his bank account?

"Chuck how much money do have?"

Chuck smirked, "A lot."

"How much is a lot?"

"Let's just say that my family and I will never go broke for many generations. If you add up everything I own I could easily be one of the richest men in the world"

Blair's mouth dropped, and she just shook her head.

"Anything I have is yours Blair, anything you want I will get it for you and your mother."

Blair smiled and walked up to him and put her arms around his neck. She pulled him down to capture his lips. He kissed her back with just as much passion as she was giving him. The stood there kissing for a while until Blair pulled away to catch her breath.

"We need to work on your breathing techniques", Chuck mumbled. Blair wasn't quite sure what that was supposed to mean so she just stayed quiet.

"Let's eat", Blair said as she sat down. "This looks so delicious, your chef is amazing."

"Yes he is, I should give him a Christmas bonus."

They settled into silence as they ate. When the meals were done, Blair finally spoke. "Chuck you haven't touched your champagne."

"That's because it's cheap and tastes horrible. Did you really pick this?" Chuck's nose scrunched up in disgust as Blair drank more.

"It tastes fine to me", Blair drank more as Chuck rolled his eyes.

"It's probably the only champagne you've had."

Blair said nothing. "Please let me chose the drinks from now on until you develop better taste."

Blair just glared at him as he got up from the table and order seven bottles of different champagne and several glasses. "Why all the champagne Bass? Addiction I should know about?"

Chuck laughed, "Yes just for something else, I'm sure you'll find out soon enough." He winked and Blair's heart sped up.  
When the champagne and glasses came Chuck picked up the boxes he'd sat down with earlier and directed her to the terrace. He pulled a chair out for her and she sat down. "Chuck Bass a gentlemen, call Nate this is front page news."

Chuck laughed, " I assure you that I do this for selfish reasons. I can get a nice look at your ass."

Blair rolled her eyes. Chuck poured each champagne in a different glass and sat the bottles next to the coordinating glass.

"Drink while we talk and figure out which one you like the best."

"Are you trying to get me drunk Bass?"

He smirked, "No, just tipsy. I want you to remember this night in the morning."

Blair smirked herself, she was sure she was going to remember this night forever. She was going to become a woman and make Chuck Bass officially hers.

She took the first glass and sipped, she didn't like and went to the next. That one was better, so she continued to sip that one.

"Waldorf you look ravishing tonight."

Blair blushed, "Thank you."

"I see I'm going to have to stop you from blushing."

Blair looked confused so Chuck explained, "When you blush it shows you are embarrassed or self-conscious. Both show weakness, and you Blair will not be weak with anyone but me."

"Why should I even be weak with you?" She asked challenging him.

"Because I won't hurt you or take advantage of that weakness. I'm on your side and you need allies. And I don't ally myself with someone who I don't know. You have to let your guards down to let me in. I want to know everything about you, the real you." He placed his hand on Blair's hand that laid on the table.

Blair looked at their hands together, they looked perfect. "Will I get the same in return?"

Chuck hesitated at first, then after a moment of silence he said yes. Blair looked up into his eyes and saw that he was being genuine.  
Blair sipped her drink then spoke, "My father abandoned my mother and me, he left us to fin for ourselves."  
"Is that why you are so determined to be powerful?"

"Partly. I want to stand on my own two feet and Blair Waldorf the woman who has it all and doesn't need anyone."

"If you want it all why don't you want someone there with you?"

"I can have it all and not have someone."

"You can't Blair, having everything is nothing without someone there to share it with. Trust me, I'm the living proof of that."

"How so?" She asked noticing the sadness in his eyes as he spoke.

"Blair I like you a lot, you've changed me in such a short amount of time it's almost scary but I'm not afraid anymore."

"Why is that?"

"Because change is inevitable, you were meant to come into my life whether I like it or not so why not embrace it? I was lonely living her by myself but I never knew it until I felt what it was like to share a home with someone. I have plenty of money and I love the pleasures that it brings but when you spend it on someone you care about it feels better. Speaking of gifts," Chuck said as he lifted the boxes to her. "These are for you Blair."

"You've done enough Chuck, why buy me gifts?"

"Because you're my girlfriend, now open up."

Blair opened the first box and laughed at what was inside, "Raina told you didn't she?"

"Yes." Inside the box were macarons of all different flavors. Blair picked one up and took a bite. She smiled it was perfection.

"Thank you, these taste so good." Blair sipped her champagne and grimaced. "Just not with this." She picked up the next glass and almost downed the drink. "I love this one, what is it?"

Chuck smirked, "Dom Pérignonis. I had a feeling you'd like that one, it's my favorite also. Although I'd rather my scotch." Chuck said as he lifted his glass of scotch up to her.

Blair smiled as she ate her macarons and drank her Dom and Chuck drank his scotch. This was perfect, just like she dreamed of.

"Chuck what was your father like?" Chuck's jaw tighted up.

"He was an asshole."

"Explain."

Chuck just looked at her but didn't explain further. Blair got up and walked over to him and sat herself in his lap. "Explain Bass, now. What happened to us knowing everything?"

Chuck sighed, "I'm sure my mother told you about him."

"I want to know how you feel personally."

"I hate him, what more do you want me to say?"

"Why do you hate him?"

"Probably the same reason you hate yours. He was there physically but he hurt my mother and wasn't there for us emotionally. He could have had it all Blair but my father was cold and heartless. He had people who loved him but he chose not to love them back, all he cared about was his business. I don't want to be like that and I don't want you to be like that either."

Blair sat silent for a while and thought about what he said. Her father had her and her mother but he chose himself. He wanted success and someone to love just not them. Blair read in the paper that he'd married someone new. The woman was not that much older than Blair and last year they had a baby together. Harold, his wife Sophie, and their son Louis were one big happy family from what Blair read. They were wealthy and living in Paris while Blair and her mother were struggling to get by.

Blair wanted to have it all but she didn't want to risk someone taking it all from her. She was happy once when she had a family and an easy life, but her father took that away from her.

"How do I know you won't leave me with nothing Bass?"

"Because Blair if I left you at all, I'd be destroying myself in the process. I may be homicidal with my attacks but I'm not suicidal."

Blair looked into his eyes and slowly lowered her head to his. They kissed gently and slowly. When Chuck pulled away Blair pouted, he laughed at her antics. "That doesn't work with me Waldorf find some other strategy."

Blair just glared at him. "Open your other present", Chuck said.

Blair turned towards the table and picked the box up. Slowly she opened it to find a velvet box. Blair hesitantly opened the lid of the box and gasped when she saw what was inside. There was a silver necklace with diamonds on it. "Chuck, this is beautiful."

"Something this beautiful deserves to be seen on someone worthy of its beauty", Chuck said as he kissed her bare shoulder.

Blair's eyes flickered shut when his lips touched her skin. "Chuck get this cleaned up and meet me in the bedroom."

Chuck looked at her with lust in his eyes. "You've been a good Bass today so hurry up and come get your reward" Blair said as she kissed her lips.

She got up from his lap and downed the rest of the Dom in the glass and picked up the bottle to bring with her into the bedroom. She was going to need it, she was nervous.

Chuck watched her as she walked to the bedroom, he was already rock hard. This was going to be amazing, he was sure of it.  
Blair made her way into the closet and shut the doors behind her. She quickly got undressed and put on the white slip she'd picked up with Raina. It was see through and made her look virginal and naughty at the same time. Blair slipped the matching thong on and let her hair down. She looked at herself in the mirror and was in awe, she looked sexy. She knew that she was going to have Chuck Bass in the palm of her hands by sunrise.

She heard the bedroom door open and knew he was finished cleaning up and waiting for her in the room. Blair quickly dranked more Dom then stood up straight and went straight for the door of the closet. She opened the door slowly to find Chuck looking at her. When he saw her clearly he felt the air leave his body.

She was stunning. The sexiest woman he'd ever seen. He could see her nipples puckered and hard under the lace material of the slip, and he saw the smooth plane of stomach. Then there was the thong that really didn't cover much because he could see right through the lace. Her mound was bare and pink.

Chuck stood planted in his spot not moving but taking in the sight before him, he wanted to remember this image forever. She slowly walked over to him and wrapped her arms around his waist and pulled him close. "Like what you see Bass?"

Chuck Bass for the first time in his life was at a lost for words, he just nodded. Blair smirked at him, "You have far too much on Bass, take it off."

Chuck watched as she walked over to the bed and crawled to the very top. She was on her hands and knees and the slip didn't cover her ass. Chuck saw her pink lips and ass and did as he was told. His pants were entirely too tight. He need to be released immediately.

Blair watched as he took off his clothes until he was left in nothing but his purple silk boxers. "Really Bass, even your boxers are purple."  
Chuck just smiled and shrugged. Blair saw that he was hard but she want to see just how hard he was for her. "Take those off too."

"After you", he replied.

"I told you to do it first, so drop them."

Chuck glared at her but did as he was told. When she finally saw Chuck's cock her mouth fell open. She was losing her confidence but getting very excited. Chuck Bass was hung, it was thick and long. She was scared and wet at the same time. Chuck smirked when he saw her expression, he got that a lot.

"Come here", she choked out.

Chuck crawled up the bed to her. "Now you take it off now, before I rip it off."

Blair gasped, that turned her on. She slid the straps down her shoulders and let the lace and silk slip pooled around her waist. Chuck wasted no time at all to attack her chest. Blair was self conscious about her breast because they were that big but the way Chuck was touching and licking them she didn't mind the size. As if he could read her mind he stopped what he was doing and said, "They are perfect Blair, they fit perfectly in my hands and my mouth." To enforce what he'd just said he took her breast into his mouth and released it slowly until just her nipple was left. He swirled his tongue around the peak and Blair's hand shot up to his head. She held him to her as he continued working her breasts with his mouth.

He pulled away, "Take it all the way off."

Blair quickly discarded the slip. "Now lay down", he commanded.

Blair did as he said. Chuck spread her legs and got in between them. He looked at her with pure passion and lust in his eyes. For the first time in her life Blair felt desireable. She reached up and pulled him flush on top of her. Blair attacked his mouth as his hands went up and down her side. He pulled away from her kiss and made his way down her neck. Blair started moaning at the fire that was left in the wake of his lips. He kissed and licked his way farther down her body until he was kissing the insides of her thighs.

He placed a wet kiss on her core and Blair grabbed his hair hard. Chuck hissed and tore the thong from her body and grabbed her hips roughly. He started licking at her core and Blair lost control of her body. She'd never felt like this before. This was heaven, Chuck was making love to her with his tongue and she was close. Chuck was enjoying the taste of Blair's pussy so much, he didn't want to stop and he wouldn't until he got her to release on to his tongue. Blair had a death grip on his head but he didn't mind the pain at all. It just egged him on. Blair's legs started to tremble as she wrapped them around his head. Chuck added his fingers into her dripping wet hole in search for her g-spot but he found something else.

When Chuck added his finger Blair couldn't hold on any longer, she fell over the edge as her body shook with her orgasm. When she was coming down from the aftermath of the orgasm she noticed Chuck was stock still in between her legs. He was trying to figure out if what he was feeling was what he thought it was. Where was no way she was a virgin and hadn't told him and who their age was still a virgin? Chuck hadn't deflowered a girl since he was seventeen.

"Chuck is something wrong?" Blair asked panicked.

"Are you.. a.. virgin?" He choked out.

Blair just looked away from him and grabbed a pillow to try to cover her now naked body. Chuck sighed and grabbed the pillow away.

"Don't cover up, I just need to know. I would've hurt you had I not known."

Blair still was silent. "Look I'm going to make this enjoyable for you, just let me know if you're sure. Stop me anytime it becomes too much to handle okay?"

Blair just nodded but didn't say a word. Chuck got up and Blair thought he was leaving and rejecting her. Tear came to her eyes but she refused to let them fall. She felt better when he came back with lit candles. He sat the candles on the night stands and took a remote from his night stand and turned the lights down.

He settled in between her legs and laid down on top of her. The feeling of his weight on her felt comforting and made her feel safe. She looked into his eyes and saw the look of pure love. She was sure her face matched his and the moment felt perfect. She thought she would've been scared in this moment but what he told her earlier and the look in his eyes made this moment feel right and comforting.

"Are you sure?"

She pulled his face down to hers and kissed him with passion. He rubbed his length against Blair's pussy coating himself with her juices, he'd left her juices on her to make sure it was well lubricated and wouldn't hurt so bad. He positioned himself at her entrance. "Blair baby this is going to hurt, tell me to stop if you can't handle it."

Blair gulped and just gripped onto his shoulders and pushed her face into the crook of his neck. Chuck kissed the side of her head as he pushed in slowly. I couldn't get far because she was very tight and he was well endowed. Chuck pulled out some and then without much warning to Blair he pushed in hard until he was all the way in. Blair's nails scratched at his back and drew blood, as she screamed in agony at the pain. Tears began falling down her cheeks. Chuck brought his hands to her face and wiped the tears away.  
He kissed her and massaged her lower back while he used ever ounce of his strength to hold still. Blair kissed him back to take her mind from the pain. As the pain subsided Blair began squirming under him. He took that as permission to move.

He began slowly, he wasn't in any rush. He was enjoying the feel of her pussy gripping his cock as he went in and out of her. Blair was feeling pure pleasure but she felt like she needed more. "Chuck please give me more", Blair said breathlessly.

Chuck smirked, "Begging are we Waldorf?" Blair just grunted and tried moving her hips to meet him and get what she was looking for. Chuck just growled and pushed his hips down on top of hers to keep them down and wrapped his arm up to grab her hair to attack her neck. He lifted his hips up some so he could drive his dick in and out of her. He was fucking her hard, Blair was screaming his name. This was what she was looking for.

Blair legs was trembling as Chuck grabbed one of her legs and lifted it up onto his forearm. He went deeper and Blair was screaming out curses.

"You like being fucked Blair?" Blair just bit his shoulder in response and yanked back his head by his hair. This just fueled him more. He was pounding Blair into the bed, she knew it would hurt in the morning but she didn't care. It felt so good, she'd never felt this way before. She felt alive and on fire. The headboard was banging against the wall and the whole bed was shaking from the force Chuck was fucking her.  
The fire in her womb was spreading and fast, she knew she was close and wasn't going to last long. Chuck knew too, and he knew he was going to be right behind her. "Blair, fuck come with me. Baby I'm not going to last much longer, you feel so good."

Chuck knew how to get them both there, he grabbed her ass and tilted her hips so that he was hitting her g-spot and he was even deeper than before. Blair screamed his name as she spasmed around him and milked every ounce of cum he had. When she screamed his name that signaled his release. He filled her womb with his seed and both of their juices dripped down her legs.

After Chuck caught his breath he rolled off of Blair and she pouted. He just chuckled at her and shook his head. He went into the closet and came out with new sheets. Blair tried to get out of bed and almost fell.  
"Blair! Are you alright?"  
She nodded. He picked her up and brought her to the bathroom. "I'm going to run you a hot bath with some vanilla and lavender to help relax your muscles so you aren't so sore in the morning." He sat her down on the toilet while he ran her bath. The steam was filling the bathroom as was the scent of vanilla and lavender. When he was done he picked her up and put her in the scolding water. She shrieked and jumped back into his arms.

"Blair, get in the tub. I'm sorry I was so rough, I just couldn't help myself..." She sighed and braced herself as he lowered her again into the hot water. Her body finally adjusted to the water and she relaxed. She smiled to herself when she thought about what he said, he'd lost control because of her. She felt accomplished and happy. He returned to the bedroom and changed the soiled sheets and laid in bed and waited for her to finish.

She came out the bathroom with her skin very red, but he still thought she looked beautiful. He still laid naked from their earlier activity. She was wrapped up in a towel and when she neared the bed he reached out and grabbed the towel from her body. "No clothes", he said simply.  
She climbed into bed naked along with him. He grabbed her and pulled her down to lay on top of him. She cuddled up into his strong hard chest and he wrapped his arms around her. The candles had burnt out and they were left in the darkness with just a bit of moonlight coming from the top of the window. Blair was wrapped up in Chuck's arms and he played with her soft curls. The fell asleep quickly with smiles on their faces.


	6. Be Bold

**I don't own Gossip Girl.**

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Chuck woke up with the sun shining into the bedroom, he slowly opened his eyes and looked around. The events of last night were clear in his mind and it caused him to smile. Usually when he bedded a girl they went home right after and he'd wake up the next morning smirking if he could remember the night at all but with Blair things were different. She stayed the night sleeping in his arms and it brought a smile to his face. He felt happy without his usual sense of cockiness.

He looked around the room for her but she wasn't there, he got out of bed and went to the bathroom to freshened up for the day then threw on his robe to go look for her. He heard noises across the hall so he assumed she was in her mother's room. He opened their bedroom door and saw that he was correct. Blair sat on the bed with her mother looking at magazines. They were both in their robes, and Eleanor was drifting asleep.

Chuck went to the door of Eleanor's room and leaned against it. He watched Blair and thought of her reading with her children someday. The thought made him freeze. The image of dark-haired children with his smirk made his mind go to last night. He tried to think hard if he used a condom or not and he realized he didn't. He paled and gasped, the noise made Blair snap her head up to look at him.

He looked like he'd seen a ghost, she tucked her mother in and walked over to him at the door. She wrapped her arms around his neck and kissed him. She noticed he was cold and wasn't kissing her back so she pulled away. "Chuck what's wrong?"

He looked at her, "Blair we didn't use a condom, I'm sorry for being irresponsible last night-"

She held her hand up to cut him off, "I'm on the pill Chuck."

He raised an eyebrow at her, "You were a virgin." He said simply.

"Yes before you changed that last night, your point is?"

"Why would a person who hasn't indulged in sex be on a pill that prevents pregnancy. You do know you must have sex to get pregnant Waldorf."

"Yes I know that!", Blair shouted and threw her hands to her mouth. She looked back to see Eleanor still sleep. She pushed him out the door and shut it behind them. When they were in the hallway she continued, "I have irregular periods from a condition I had."

Chuck looked at her with curiosity in his eyes, Blair realized she'd said too much. She pushed pass him and walked into the room, but she felt Chuck follow her.

"What condition Waldorf?"

"The condition that's none of your business."

"I'm your boyfriend, it is my business, so spill now", he commanded as they both stepped into the bathroom. He locked the door behind them.  
Blair looked over her shoulder at him and sighed, "I really don't want to talk to you about it. Serena and Dorota are the only ones who know."

"I want to help you Blair, tell me. I won't judge you."

Blair turned to face him and looked down, "I had bulimia."

"Do you still do that now?"

"No."

"Good", he said as he walked over to Blair and crushed his lips to her. "If you ever do feel the need to do that again Blair come to me, I don't care what I'm doing or where I am. Come to me."

She nodded. "I'm going to take care of you and Eleanor from now on, so when there's a problem just come to me", he added on.

Blair kissed him and went to grab his back when he winced in pain. Blair pulled away quickly. "What's wrong?"

"My back is full of scratches from last night."

"I'm sorry about that."

"Don't worry about it Waldorf, I enjoyed every single last bit of it", he said as he stalked towards her and pinned her against the bathroom door.

He kissed her until she was breathless then pulled away, "Are you still sore?"

"A little, but mostly just aching muscles."

He pulled the tie that was holding her robe closed and slide the robe from her body. She was naked before him and he took in the sight of her skin.

She felt uncomfortable under his glaze, she didn't have nothing to hide her imperfections from him. She began to blush when he looked at her pussy. Chuck noticed the red tint to her skin when he looked up into her eyes. "Blair what are you embarrassed for?"

"The way you're looking at me."

"You are beautiful like a work of art, you should be carefully appraised my dear. I think you're embarrassed because I looked here." He said as he ran his fingers along the folds of her pussy.

Blair gasped and her eyes almost fluttered shut as wetness flooded from her core. Chuck felt her juices on his fingers, he brought them to his mouth and tasted her. She sat staring at him getting turned on.

He picked Blair up and put her on top on the sink counter. He kneeled down and became frustrated when she was that Blair sat with her legs closed. He pulled her legs apart and he his face was directly in front of her pussy. Blair blushed again and looked away.

"Blair when you are with me your legs open and they open only to me", he said as he kissed her pussy. "Is that clear?"

"Yes", she moaned.

He pulled away, "Next thing, you will stop blushing when I look at your pussy. It is mine right?" he asked her as he licked it.

"Yes, it's your Chuck", she screamed in pleasure.

He moved away again and she groaned. "Don't be shy around me Blair, you're beautiful and I like to admire things of beauty."

He got up and went over to the tub and turned on the water. Blair looked at him like he'd got crazy. She was now turned on and want him.

"Chuck?"

"Hmm?" was all he said. He didn't turn around to look at her.

"What are you doing?"

"Running you a bath, what does it look like I'm doing. You're sore." He said innocently even though he had a smirk on his face that Blair couldn't see.

"I thought you were doing something else", she said very frustrated.

"And what's that?" he asked almost laughing when he turned around and saw her look of frustration.

"Nothing, forget about it", she said rolling her eyes. She got down from the sink and walked over to the tub where he stood.

He said pouting didn't work on him so she needed something that did. She needed to find a way to break Chuck down to get what she wanted from him. She was still uncomfortable with her body but he seemed to like it so with all the courage she had she bent down still naked and ran her hand through the water that was filling the tub.

She saw out the corner of her eye that Chuck was watching her ass with hooded eyes. "What are you doing Waldorf?"

She smirked, her plan was working. "Just checking the water to make sure it's not too hot. It's just right though. You always do things just how I like it Chuck." She said as she stood and pressed her body up against his. Her naked breast rubbed up against the soft silk of his robe and she moaned but she never took her eyes off his. He shut his eyes and his breath hiked, Blair could feel his dick getting hard.

"Well I do like to please you", Chuck said playing along with her wanting to get more of the vixen out of her. He liked her bold and not shy, she needed to be bold to be on the top. "You want me to please you Blair?"

Blair just nodded and Chuck shook his head, "No Waldorf say it." He said as he smacked her ass firmly. Blair gasped at the subtly of it and gripped his robe.

"Tell me what you want B, ask and I will give it to you. Anything you want I'll get, anything you ask of me I'll do. All you have to do is say the words. Be strong

Blair," he said as he grabbed her ass hard and pulled her more to him. His erection was becoming even more noticeable.

"Take your robe off", Blair said quietly.

Chuck raised an eyebrow, "I can't hear you. You can speak louder than that I know you can. Come on Waldorf the room is sound proof, put more bass in your voice."

"Take it off now Bass!" Blair screamed and Chuck smirked at her as he complied to her wishes.

"Is that all you want B?"

She shook her head.

"Well, what is it that you want? Is it anything you see in front you?" Chuck egged her on.

"I want you to lick me down there", Blair spoke hesitantly and looked down to the ground.

He smirked then turned to the tub to turn the water off so it didn't overflow then turned back to Blair. Chuck was going to make her into a sex goddess, and he was going to have fun doing it. He lifted her up on the counter where she was before and he once again dropped down to his knees.

"What is it that you want me to do again?" Chuck asked.

"Lick me down there."

"Here?", he asked as he kissed her ankle.

"No", she answered with a look of annoyance on her face. "You know where Chuck."

"Here?", he asked as he kissed her knees.

"No! Further up, now Bass."

"Here?", he asked as he kissed her inner thighs. Blair moaned at the feeling but it wasn't what she wanted.

She grabbed his hair hard and yank his head up so it would be right where she wanted it but he pulled his head from her leaving his breath blowing hot against her core. "Bass!", Blair screamed in angry. "If you don't eat my pussy at this very moment I'm going to go find someone else to do it."

Chuck growled then put his mouth where she wanted it. He licked at her pussy slowly but firmly. He became to massage her inner thighs to release the tense from last night. He alternated from licking at her clit to fucking her with his tongue. He could tell Blair was close when his name fell constantly from her lips. He added to fingers inside of her and began pressing against her g-spot and sucking on her clit simultaneously. Blair came violently as her walls gripped Chuck's fingers tightly. He drank all her juices and placed a kissed on her lower lips.

He stood up and his face was glistening from her. "Now what where you saying about going find someone else?"

"Nothing", Blair said breathlessly as she shook her head. She would never get enough of that. She grabbed his head and pulled him to her for a kiss. She explored his mouth with her tongue loving the taste of herself on him. He was rock hard and his erection was laying on top of her thigh.  
She grabbed it and guided it into her slowly until it was half way in, then Chuck pushed it in the rest of the way making them both gasp. Blair dropped her head to his shoulder and whispered against his neck,"Chuck fuck me."

"Blair let me make love to you."

Blair lifted her head up from his shoulder and looked into his eyes. "Chuck.. I don't know what to say... We just met a few days ago you couldn't possible love me already.. can you?"

"Blair I know you felt it last night, I believe you were meant to be in my life. I think we're inevitable, I've never believed in love until you came along. You've made me change my whole life with just your presence. You've turned me into someone who could love and I don't know how Waldorf. You've shown me that I am capable to be kind, loving, and compassionate. All I've ever wanted was to be a better man than my father and you've given me the power to do so. When you fell asleep in my arms I felt whole for the first time in my life. Having you and Eleanor here makes me happy, it feels like I finally have a whole family. Blair Waldorf I love you, say you love me too."

Blair had tears in her eyes, "Chuck I felt it too. I thought that losing my virginity to you would've been something I'd regret but it was perfect. It felt so right and I'm so glad that I lost it to you. It feels like I've waited so long just for you but I didn't know it. I love how you make me feel safe and warm inside. When my father left my mother I lost my belief in love but you've restored it. I know you love me Chuck I can feel it whenever you're around. I'm so happy to be your family, you are a kind man and I'm happy to be the one to show you that you are. I love you Chuck Bass, please don't hurt me."

"I won't Blair, I promise I will never hurt you intentionally. Promise me that we'll stand by each other through anything. Our darkest thoughts, the worst things we can ever do. We will stand by each other through it all."

"I promise. Now shut up and make love to me Chuck Bass."

Chuck crushed his lips to hers and slowly pulled out and then back in. He moved slowly and Blair didn't mind at all. Their love for each other was consuming and it made their nerves stand on end. Chuck was pouring his heart into his strokes. They were strong but passionate and it was burning Blair alive from the inside. Her whole body felt like it was on fire but the heat felt good.

He grabbed her ass and pick her up and walked over to the tub. The tub was big enough for him to sit down and have Blair straddle him. Blair sat there on top of him and just looked at him. Chuck was confused, "Blair what's wrong?"

"I don't know what to do..." Blair said looking down away from his eyes and started to play with his chest hairs.

Chuck grabbed her hips, "It's okay Blair, you were a virgin before last night. I'll teach you what to do. You're a blank canvas and I plan to have fun filling you with every single sexual thing I know."

Blair grabbed his shoulders and pulled him to her face, "I'm looking forward to it lover." She said huskily.

Chuck pulled back to look at her face, "That's what I like to hear, never hold back with me. When it's me and you let loose."

He picked her up so she was almost all the way off him, "Sit back down." He commanded.

Blair slammed herself down and she moaned at the pleasure of him being deeper than ever before.

"How does that feel Blair?"

"So good, it's so deep."

"You like it deep B?"

"Yes Chuck, I like it deep."

"Well do it again, but do it harder."

He lifted her up again and she slammed back down. She clawed at his chest when his hands moved down to her ass and dug deep into it.

"Harder!" he barked at her as he lifted her up again.

She slammed back down with all the strength she had and she was rewarded with the pleasure of him filling her.

"Now you pick yourself out."

Blair looked at him hesitantly. "Now Waldorf!", he said forcefully as he palmed her breast roughly.

Blair's head dropped back and she arched into his hands as she lifted herself up and then dropped back down.

"Good girl", Chuck said as he popped one of her nipples into his mouth. Blair moaned at the feeling.

"Do it again Blair, and don't stop until you're coming all over my cock."

Blair just grabbed the back of his head with one hand to hold him to her chest and grabbed the side of the tub to give her levearge with the other.

She pulled herself up and slammed herself down repeatedly, Chuck was helping by grabbing her ass and guiding her up and down on his dick. The feeling of the water slapping around them felt good. Blair was close and so was Chuck. She pulled his head up to hers and kissed him deeply. Chuck then slid them down farther into the water and began meeting her thrust. Blair screamed, "Chuck you're so big, ahhh fuck me Chuck fuck me."

Hearing Blair talk dirty made Chuck explode with a powerful thrust and Blair was right behind him. Her walls gripped his twitching dick tightly and milked him for every last drop her his seed. Chuck pumped twice more then went limp beneath a limp Blair.

"That was so good, I want to do that again", Blair said.

Chuck laughed, "As much as I would love to take you again, we have to get cleaned up and dressed."

"Why? Are we going somewhere?"

"Yes, we're meeting Nate and Serena lunch then we're going to the bank to get your card so you can order a new cell phone tonight."  
Blair kissed him and then they washed each other off and went into the room. They walked into the closet together and helped each other get dress. Blair was fixing Chuck's tie when she thought of something. "Chuck who's going to watch my mother while we're gone?"

"I'll have a nurse come sit with her, it's no problem."

"If Dorota finds out another nurse was here she'd have a fit", Blair said laughing.

"Well call up Dorota and have her sit with Eleanor, I'll pay her whatever she wants."

"That'll work", she said as she got the tie straight and neat.

Chuck and Blair were in the limo an hour later headed to Emerald's for lunch. When they walked in they found Nate and Serena looking very cozy in a booth.  
Serena saw them first, "Hey B, Chuck!"

Blair walked over to her best friend and hugged her. "Hey Nate."

"Blair", he said with a nodded and lopsided smile.

Blair scooted into the booth and Chuck followed her.

"So Nate when's the next feature on Blair and me?"

"In a few minutes if you agree with the article. I'd say it's pretty nice, your employees got some nice pictures", Nate said as he handed over a piece of paper to Chuck.

Chuck took it and put his arm around Blair and leaned into her and put the paper between them so they both could read it.

"There was a romantic dinner set up in the Bass penthouse last night for the one and only Chuck Bass. We hear there was champagne, gourmet food, and lots of sweets in the Bass penthouse for Chuck and his mystery girl. Has he traded in his debauchery for domestics?" There was a picture of the their living room from their romantic dinner with Blair walking to the rooms. You couldn't see her face, just the back of her.

Blair smiled and Chuck just nodded and handed the paper back to Nate.

"Why is Blair a mystery girl? Don't you want people to know her?" Serena asked after looking over the paper.

"She isn't ready for this world yet, she has a lot to learn about the people of the Upper East Side before she can be among them yet alone lead them. She looks the part but one minute alone with one of the pretentious assholes and they'd crush her. I'd like to keep her name out of things while I toughen her up and get her mentally ready to face this world." Chuck explained.

Serena looked confused but she just nodded. "So are you two dating for real?" Serena asked almost squealing.

Blair smiled brightly, "Yes. There so much we have to talk about S, maybe we can go shopping after I get my card."

"Card?" Serena asked confused.

"Yes, Chuck's getting me a bank card."

Nate just looked at Chuck and raised an eyebrow, but said nothing. Chuck just pulled Blair closer to him.

Nate, Chuck, and Serena's phones went off. It was the Spectator, none were surprised at that but when Nate looked at the number of looks the post got he was surprised. "Wow 2,000 looks already, who knew someone's relationship would be so interesting."

Chuck smirked, "Well I am Chuck Bass and Blair has made the impossible happen."

"Chuck Bass with a girlfriend, who would've ever thought this be possible."

"Not I", Chuck said as he kissed the side of Blair's head.

The four friends ate while they laughed and caught up.

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** I really didn't know how to end this chapter, I know the end sucks but I still hope you like the chapter. Next chapter Nate and Chuck will talk and Blair and Serena will talk.**


	7. Helping Out a Friend

**I don't own Gossip Girl.**

* * *

After lunch the four friends got into Chuck's limo and set off to the bank. Chuck went in and came out five minutes later, while the rest of the gang sat in the limo. When he got in he handed Blair a black card, she grabbed the card gently like it would break if she pressed on it too hard. Chuck laughed, "Blair it's okay it won't break, and if it does I'll just get you another one."

Blair looked at Chuck, "It's so shiny and pretty, I always don't want to touch it let alone swipe it."

Serena went to grab the card from her, "Well then I'll swipe it for you." Blair quickly moved her hand away and glared at her, "You will do no such thing, this is my baby."

She turned to Chuck, "What is the limit on this thing?"

Nate laughed and Chuck just smirked. Blair didn't find anything amusing, "What's so funny Nate?"

He held his hands up in surrender. She glared for a little while longer than turned back to Chuck for an answer.

"Blair there is not limit, buy whatever your heart desires", he said as he played with a strand of her hair.

"I could buy whatever I want?" She asked curiously, she was excited by this.

"Yes my love, anything."

"I can pay for my tuition?"

"You can buy Yale if you wanted to."

Blair eyes got big, she had what she always wanted in the palm of her dainty hands. Hands that worked to barely get by now held the key to the future she'd always wanted.

Blair looked up into Chuck's eyes, "I love you Chuck."

"I love you too Blair", he said softly as he kissed her. There was a flash that made them pull away. They turned to find Serena smiling brightly holding a camera. Chuck and Blair glared at her and she quickly put the camera down.

"What it was a Kodak moment", she said looking at her lap.

Nate put his arm around her shoulder and pulled her to him and kissed her temple. "It's okay babe, they have to get use to paparazzi sooner than later and if we have shots of intimate moments like this the Spectator will be ahead of everyone."

Chuck rolled his eyes, "Nate you already have my hotel employees on your pay roll how many shots do you really need? What's next

"Relationship Advice for Chuck & Blair" love column?"

Nate seemed to think about it, Chuck glared. "I was kidding Nathaniel."

"I know, but it could be good. Love advice from Manhattan's Bad Boy reformed."

"I'd never be caught dead writing a column, keep dreaming" Nate just shrugged.

The limo pulled up to the Empire and Nate and Chuck stepped out.

"Blair, have fun today. Don't worry about the money, it you see something you like buy it." Chuck said as he kissed Blair.

"Don't worry I'll make sure we shop until our hands get tired from swiping", Serena said as Chuck shut the door.

Nate laughed, "You know Serena is going to get a new wardrobe on you right?"

"I know, but you're going to offer Blair a job once she get's settled."

"Doing what?"

"Running the magazine you're about to launch under the Spectator."

"You're buying her a magazine? Wow man you really are in love."

Chuck just shrug but he couldn't help but smile at that. Chuck Bass was in love, and it was all because Blair Waldorf. He was finally changing into a good person and he liked it.

Chuck and Nate went up to the penthouse and poured themselves a drink and played pool while Dorota took Eleanor to the park for the day.

"Man I don't know what I'm going to do about Serena", Nate said sitting on the couch sipping his scotch.

"What do you mean? Is there trouble in paradise?"

"Well no, not exactly. I just want her to move it with me but she doesn't want to."

"Well excuse my bluntness but isn't she a prostitute Nathaniel? You're rich, she should be rushing to move in with you."

"She doesn't want me to take care of her but do you think that's why Blair agreed to move in with you?"

Chuck thought about this for a second. Maybe at first she did but he'd open up to her and she apparently liked what she saw. She gave him her virginity and didn't regret it. Chuck hadn't forced her to have sex with him nor said it was a requirement for the deal. She said she loved him and opened up to him about her life. This wasn't about the deal anymore, things had become real and true.

Chuck smiled at his friend, "No maybe at first but now it's a real relationship."

"Well I wish Serena was take notes from Blair and want to be pampered."

"I don't pamper Blair, she'd head strong. She wants to be independent and able to stand on her own. That's why I want her to have a job so she doesn't feel like she's dependant on me. I would love to spoil Blair but she'd never be happy in my shadow, she wants to be her own person."

"So you're saying get Serena a job?"

"Yes Nathaniel, it's that simple."

"She'd never take a job at the Spectator and who's going to hired an ex-prostitute?"

"I'll hire her, she can be my PR. I'll set up the interview on Monday just send her here. I'll be working from my home office for a while."

"Okay.. Wait why are you working from home?"

"I need to groom Blair for this world Nathaniel, and the sooner she's done with her lessons the better. I can already tell that she's a fast learner and will be a fierce socialite."

"What are you going to teach her?"

"Etiquette, blue blood history, war tactics. Things of that nature."

Nate raised an eyebrow, "War tactics?"

"Nathaniel she must know how to protect the kingdom, in order for her to be Chuck Bass' girlfriend she has to up to par with my war antics. I need her to pull her weight in my schemes, we're partners in this."

Nate shook his head, "I'll just stay on the sidelines and continue to watch."

Serena and Blair were sitting at a booth of a restaurant sipping lemonades and catching up.

"Oh my god Blair you boned him!?"

Blair shhed her friend and stared at her angrily, "Shut your mouth Serena!"

"Oops, sorry..." Serena said looking around before looking at Blair offering a weak smile. "So did you bone him?"

Blair rolled her eyes, "We made love Serena, and it was the most magical thing ever. I thought it was the fourth of July by all the fireworks I've seen."

"Is it big?"

Blair scoffed, "Have you no shame Serena really?!"

Serena didn't look fazed at all, "So it's small?"

Blair glared at her and looked around before saying, "No it's not small, it's quite big actually."

"On a scale to baby carrot to salami what is he?"

"Salami..."

Serena's eyes bugged out, and her and Blair both laughed. "I've missed you so much B. I need your advise on something."

"What is it S? Is Nate a baby carrot?"

Serena laughed, "No he's a cucumber" she giggled. "It's just that he wants me to move in with him."

"And?"

"I don't want to."

"Why not? I thought you wanted to be famous, who better to make you an It-Girl than Nate? He runs a newspaper for crying out loud."

"I know I said I wanted to be famous, I do want to be famous... it's just that I want to be famous and make my own money. I don't want to be like my mother and have to marry husband after husband to get by."

"Well get a job."

"I'm an ex-prostitute Blair, no one will actually hire me."

"You'll find a job S, I'm sure Nate could find you a job."

"I don't want to be banging my boss!"

"Chuck could help, he does own half of the city."

"Chuck doesn't know me like that, why would he do that for me?"

"Well for one because you're dating his best friend and second because he's sleeping with your best friend and I'm working on perfecting the perfect weapon against Chuck." Blair smiled to herself thinking of this morning.

"You were just a virgin now you can't even go a few hours without thinking of him, B is the sex that good?"

"If you must know it is Serena, he is Chuck Bass."

"He probably have a sex dungeon locked away somewhere that has virgins lined up waiting for him to deflower them," Serena laughed but Blair just sat with a blank face. Serena stopped laughing, "Sorry, not funny I guess."

"No it is not funny, I don't even want to begin to think of how many woman he's been with."

Serena shuddered, "Especially on his and Nate's lost weekends alone."

"Evelyn told me of those lost weekends, are they really that bad?"

"What do you mean by bad?"

"What really goes on at these lost weekends?"

"They drink, do drugs, and fuck girls. It's pretty simple."

"Do you know when the last time Chuck went was?"

"I wasn't really paying attention to Chuck at the last party, it's not like we were all sitting around braiding each other's hair. I was working."

"I'm sure it wasn't work at all."

"I can't remember, it was a long time ago."

Blair sat back in her chair, "Good... Serena let's go shopping for some lingerie so I can thank Chuck tonight for my new clothes and yours." Blair said as she rolled her eyes and Serena giggled.

They arrived at the Empire two hours later laughing with a lot of bags. Chuck and Nate were watching a movie smoking a joint. Serena went and sat right in Nate's lap.

"Natey I had so much fun today but I'm tired, can we go back to your place?" She asked Nate.

"Okay babe, Chuck wants to talk to you about something though. Talk to him and I'll be waiting in the car for us to go home I'll bring the bags down." He turned to Blair who was coming out of the bedroom. "Goodnight Blair, see you later Chuck." He said as he grabbed as many bags as he could and went into the elevator.

Chuck put the joint out and stood up, "Blair dear I'm going to go have a word with Serena in my office for a minute, we'll be right out." Just then Dorota and Eleanor came through the elevator.

"Well now that mother's here I'll get her ready for bed then go get the bed ready for us", Blair said with a sly smile. She turned around to walk away and Chuck grabbed her ass.

"Waldorf you might want to stretch while I'm gone", he said as he motioned for Serena. He turned around on his way to the office. "Oh and Blair go to the closet and open the door all the way in the back and pick out a movie for us to watch tonight."

Blair raised an eyebrow but turned and went to tend to her mother, she figured he'd just want to watch a movie when they were done.  
Chuck sat down behind his desk and waited for Serena to sit in front of it.

"What is this about?" Serena asked uncomfortably.

"Relax, I won't bite" he said chuckling. "Well not you at least."

"Eww, can you get to the point please. Nate's waiting in the car and your sexual need for Blair is heavy in the room."

"Okay I'll cut to the chase, I want you to come to a job interview for Bass Industries Monday."

Serena's mouth fell open, "Are you serious?"

"Yes, and I'm not really asking I'm tell. Come here Monday morning at 10 and my secretary will interview you for the job."

"What kind of job?" Serena asked smiling.

"I want you to be my PR, if you do a good enough job you could be the PR of the company."

"Oh my god Chuck thank you!", she screamed as she ran around his desk and hugged him.

He stood still shocked that she'd moved so fast and her excitement. He patted her back, "No problem but if you'd excuse me. I hate to be rude but I have somewhere I have to be."

Serena quickly released him from her arms and turned towards the door. "Sorry, go to Blair. I'll see you on Monday, and thank you so much!"

Chuck nodded and followed her out the door and watched as she got into the elevator jumping up and down happily. Chuck noticed that Eleanor's door was open and the light was off so he walked in and saw that she was sleeping. He walked over the her and placed a kiss on her cheek and then silently closed the door. He walked into the bedroom and saw that Blair was in the closet looking into the door that held his collection. He smiled as he walked in behind her and wrapped his arms around her.  
She turned around in his arms and gave him a lustful look, "Bass what is this?"

* * *

**This is probably a short chapter but I need it to set up the rest of the story's plot. Up next will be Serena's first day at work and Blair's first lesson.**


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